Substituted 4-cyan-3-phenyl-4-(pryridine-3-yl)butanoates, processes for preparation thereof and use thereof as herbicides and plant growth regulators

ABSTRACT

Substituted 4-cyano-3-phenyl-4-(pyridin-3-yl)butanoates, processes for their preparation and their use as herbicides and plant growth regulators 
     Compounds of the formula (I) or salts thereof 
     
       
         
         
             
             
         
       
     
     in which R 1  and (R 2 ) n  are as defined in claim  1  are suitable as herbicides for the control of harmful plants or as plant growth regulators. 
     The compounds can be prepared by the processes of claim  7.

The invention relates to the technical field of the herbicides and plantgrowth regulators, preferably the herbicides for controlling unwantedvegetation or the herbicides for the selective control of broad-leavedweeds and weed grasses in crops of useful plants, or the plant growthregulators which can be used for influencing the growth of crop plants.

In their application, crop protection agents known to date for theselective control of harmful plants in crops of useful plants or activecompounds for controlling unwanted vegetation sometimes havedisadvantages, be it (a) that they have no or else insufficientherbicidal activity against particular harmful plants, (b) that thespectrum of harmful plants which can be controlled with an activecompound is not wide enough, (c) that their selectivity in crops ofuseful plants is too low and/or (d) that they have a toxicologicallyunfavourable profile. Furthermore, some active compounds which can beused as plant growth regulators for a number of useful plants causeunwanted reduced harvest yields in other useful plants or are notcompatible with the crop plant, or only within a narrow application raterange. Some of the known active compounds cannot be producedeconomically on an industrial scale owing to precursors and reagentswhich are difficult to obtain, or they have only insufficient chemicalstabilities.

In the case of other active compounds, the activity is too highlydependent on environmental conditions, such as weather and soilconditions.

The published patent applications EP-A-5341, EP-A-266725, EP-A-270830,JP-04/297454, JP-04/297455, JP-05/058979, WO 2011/003775, WO2011/003776, WO 2011/042378, WO 2011/073143 and WO 2011/098417 discloseherbicidal cyanobutyrates.

EP-A-5341 describes herbicidal esters and amides of4-cyano-3,4-diarylbutanoic acids. The aryl radicals mentioned areoptionally substituted phenyl radicals and unsubstituted pyridyl orthienyl. The specific examples include mainly4-cyano-3,4-diphenylbutanoic acids and esters. There are two specificexamples of compounds containing pyridyl, namely4-cyano-3-phenyl-4-(pyridin-3-yl)butanoic acid and the correspondingethyl ester.

According to EP-A-5341, the threo isomers are generally suitable for thenon-selective control of harmful plants, whereas the erythro/threoisomer mixtures are suitable for the selective control of harmful plantsin some crops of useful plants. Moreover, EP-A-5341 mentions that the 2enantiomers belonging to the threo form differ in their activities,which was studied in an exemplary manner using the different activitiesof the enantiomers of the enantiomer pair of4-cyano-3,4-diphenylbutanoic acid having unsubstituted phenyl radicals.

EP-A-266725 discloses a number of erythro/threo isomer mixtures of4-cyano-3,4-diphenylbutanoic acids and derivatives thereof which can beused selectively for the control of weeds in rice crops.

EP-A-270830 describes that threo isomers and erythro/threo isomermixtures of 4-cyano-3,4-diarylbutanoic acid (esters) can be used asplant regulators, preventing the development of an infructescence invarious harmful grasses. The aryl radicals mentioned are optionallysubstituted phenyl radicals and unsubstituted pyridyl orhalogen-substituted pyridyl. Specific examples relate mainly to(substituted) 4-cyano-3,4-diphenylbutanoic acid (esters). Additionallydescribed are also 4-cyano-3-pyridyl-4-phenylbutanoic acid esters, suchas the compound ethyl 4-cyano-3-pyridyl-4-phenylbutanoate, or4-cyano-3-phenyl-4-pyridylbutanoic acid ester, such as the compoundmethyl 4-cyano-3-(4-chlorophenyl)-4-(6-fluoropyridin-3-yl)butanoate.JP-04/297455 discloses herbicidal 4-cyano-3-phenyl-4-heteroarylbutanoicacid (esters), where the heterocyclic radicals are selected from thegroup consisting of 1,2,4-triazolyl, 1-pyrazolyl, 1-imidazolyl, 2- and3-thienyl, 2- and 3-pyridyl, 1-methylpyrrol-2-yl, 2-quinolinyl,2-methyl-3-trifluoromethylpyrazol-5-yl and5-trifluoromethylpyridin-2-yl. Specific compounds from the 3-pyridylseries only comprise unsubstituted pyridin-3-yl radicals, for examplethe compounds propargyl and allyl4-cyano-3-phenyl-4-(pyridin-3-yl)butanoate.

WO 2011/003775 discloses specific esters of 4-cyano-3,4-diphenylbutanoicacids which can be used as effective herbicides, preferably also incrops of useful plants.

WO 2011/003776, WO 2011/042378, WO 2011/073143 and WO2011/098417disclose 4-cyano-3,4-diphenylbutanoic acids and esters which havespecific substitutions at the phenyl radicals and can be used aseffective herbicides, preferably also in crops of useful plants.

The herbicidal activity of the known compounds of the class ofsubstances mentioned, in particular at low application rates, and/ortheir compatibility with crop plants remain deserving of improvement.

For the reasons mentioned, there is still a need for alternative, highlyactive herbicides for the selective application in plant crops or use onnon-crop land. It is also desirable to provide alternative chemicalactive compounds which may be used in an advantageous manner asherbicides or plant growth regulators.

Likewise desirable are compounds having herbicidal activity which arehighly effective against economically important harmful plants even atrelatively low application rates and can be used selectively in cropplants, preferably with good activity against harmful plants.

Surprisingly it has now been found that certain compounds ofheterocyclically substituted cyanobutyrates have particular herbicidalactivities and can preferably be employed selectively in some crops forcontrolling harmful plants.

The present invention provides compounds of the formula (I) or saltsthereof

in whichR¹ represents hydrogen or a hydrolysable radical, preferably

-   -   R¹ represents hydrogen or an optionally substituted hydrocarbon        radical or an optionally substituted heterocyclyl radical, where        each of the two last-mentioned carbon-containing radicals        including substituents has 1 to 30 carbon atoms, preferably 1 to        24 carbon atoms, in particular 1 to 20 carbon atoms,    -   or    -   R¹ represents a radical of the formula SiR^(a)R^(b)R^(c),        —NR^(a)R^(b) or —N═CR^(c)R^(d), where in the 3 last-mentioned        formulae each of the radicals R^(a), R^(b), R^(c) and R^(d)        independently of the others represents hydrogen or an optionally        substituted hydrocarbon radical, where, however, SiH₃ for        SiR^(a)R^(b)R^(c) is excluded, or R^(a) and R^(b) together with        the nitrogen atom of the group —NR^(a)R^(b) represent a 3- to        9-membered heterocycle which, in addition to the nitrogen atom,        may contain one or two further ring heteroatoms from the group        consisting of N, O and S and which is unsubstituted or        substituted, or R^(c) and R^(d) together with the carbon atom of        the group —N═CR^(c)R^(d) represent a 3- to 9-membered        carbocyclic radical or a heterocyclic radical which may contain        1 to 3 ring heteroatoms from the group consisting of N, O and S,        where the carbocyclic or heterocyclic radical is unsubstituted        or substituted,        -   where each of the radicals R^(a), R^(b), R^(c) and R^(d)            including substituents has up to 30 carbon atoms, preferably            up to 24 carbon atoms, in particular up to 20 carbon atoms,            or    -   R¹ represents a radical of the formula —C(═O)—R^(e) or        —P(═O)(R^(f))₂ where R^(e) and R^(f) independently of one        another each represent hydrogen, OH, (C₁-C₈)-alkyl,        (C₁-C₄)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,        (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₈)-alkyl,        (C₁-C₆)-alkoxy-(C₁-C₈)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl,        (C₁-C₄)-haloalkoxy-(C₁-C₈)-alkoxy, (C₃-C₈)-alkenyloxy,        (C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl,        (C₃-C₈)-alkenyloxy-(C₁-C₈)-alkoxy, (C₃-C₈)-alkynyloxy,        (C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl,        (C₃-C₈)-alkynyloxy-(C₁-C₈)-alkoxy, —NR*R**, where R* and R** are        defined further below, tri-[(C₁-C₄)-alkyl]silyl,        tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)-alkyl, (C₃-C₆)-cycloalkyl,        (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl,        (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₆)-cycloalkenyl,        (C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl,        (C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkoxy, (C₅-C₆)-cycloalkynyl,        (C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl,        (C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkoxy, phenyl,        phenyl-(C₁-C₈)-alkyl, phenyl-(C₁-C₈)-alkoxy, phenoxy,        phenoxy-(C₁-C₈)-alkyl, phenoxy-(C₁-C₈)-alkoxy, phenylamino,        phenylamino-(C₁-C₈)-alkyl, phenylamino-(C₁-C₈)-alkoxy, a radical        Het¹, Het¹-(C₁-C₆)-alkyl, Het¹-(C₁-C₆)-alkoxy,        Het¹-O—(C₁-C₆)-alkyl or Het¹-O—(C₁-C₆)-alkoxy,        -   where each of the 23 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B),    -   (R²)_(n) represents n substituents R²,        -   where R², if n=1, or each of the substituents R², if n is            greater than 1, independently of the others represents            halogen, cyano, nitro, hydroxy, (C₁-C₈)-alkyl,            (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy,            (C₁-C₈)-alkylthio, (C₁-C₈)-alkylsulphinyl,            (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkyl,            (C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio,            (C₁-C₆)-haloalkylsulphinyl, (C₁-C₆)-haloalkylsulphonyl,            (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,            (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl,            (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy, (C₃-C₆)-cycloalkyl which            is optionally substituted by one or more radicals from the            group consisting of halogen and (C₁-C₄)-alkyl,            (C₃-C₆)-cycloalkoxy which is optionally substituted by one            or more radicals from the group consisting of halogen and            (C₁-C₄)-alkyl, or a radical of the formula C(O)OR³,            C(O)NR⁴R⁵, C(O)—Het², NR⁶R⁷ or Het³        -   or where in each case two groups R² located ortho at the            ring together are a group of the formula -Z¹-A**-Z² in which        -   A** represents an alkylene group having 1 to 4 carbon atoms            which is optionally substituted by one or more radicals from            the group consisting of halogen, (C₁-C₄)-alkyl,            (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,        -   Z¹ represents a direct bond, O or S and        -   Z² represents a direct bond, O or S, where the group            -Z¹-A**-Z² together with the carbon atoms, attached to the            group, of the phenyl ring form a fused-on 5- or 6-membered            ring,

-   R³ represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned below,    preferably (C₁-C₄)-alkyl,

-   R⁴, R⁵, R⁶ and R⁷ independently of one another each represent    hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, where    each of the 3 last-mentioned radicals in each case independently of    the others is unsubstituted or substituted by one or more radicals    from the group consisting of halogen, nitro, cyano and phenyl which    is optionally substituted, preferably unsubstituted or substituted    by one or more radicals from the group consisting of halogen, nitro,    cyano, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, or    -   (C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentioned        radicals in each case independently of the other is        unsubstituted or substituted by one or more radicals from the        group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl,    -   (C₁-C₄)-haloalkyl, phenyl and benzyl, where each of the 2        last-mentioned radicals is optionally substituted, preferably        unsubstituted or substituted by one or more radicals from the        group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl and        (C₁-C₄)-haloalkyl,

-   Het¹ independently of the others in each case represents a    saturated, partially unsaturated or heteroaromatic monocyclic    heterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-membered    bicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms    selected from the group consisting of O, N and S,

-   Het² and Het³ independently of one another each represent a    saturated or partially unsaturated radical of a heterocycle having 3    to 9 ring atoms and at least one nitrogen atom as ring heteroatom at    position 1 of the ring and optionally 1, 2 or 3 further ring    heteroatoms from the group consisting of N, O and S, where the    radical of the heterocycle at the nitrogen atom in position 1 of the    ring is attached to the remainder of the molecule of the compound of    the formula (I) and where the heterocycle is unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo, preferably the    radical of a saturated heterocycle of the type mentioned, in    particular a morpholino, piperidino or pyrrolidino group,

-   R*, R** independently of one another (and also independently of    other radicals NR*R**) each represent H, (C₁-C₈)-alkyl,    (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₆)-alkanoyl, [(C₁-C₄)-haloalkyl]carbonyl,    [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkylcarbonyl, phenyl, phenylcarbonyl,    phenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkylcarbonyl, where each of    the 7 last-mentioned radicals is optionally substituted in the cycle    by one or more identical or different radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy or, in the case of saturated    cyclic base groups, also oxo, or

-   R* and R** together with the nitrogen atom represent a 3- to    8-membered heterocycle which, in addition to the nitrogen atom, may    contain one or two further ring heteroatoms from the group    consisting of N, O and S and which is unsubstituted or substituted    by one or more radicals from the group consisting of (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl and oxo,

-   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,

-   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₈)-alkyl,    (C₁-C₆)-haloalkyl, cyano-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkyl,    nitro-(C₁-C₆)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl,    (C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy,    (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy,    (C₁-C₈)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,    (C₁-C₈)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,    (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the    formula R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)-alkyl, the radicals    R^(aa) being defined further below, —NR*R**, R* and R** being    defined further below, tri-[(C₁-C₄)-alkyl]silyl,    tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl,    phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino,    phenylamino-(C₁-C₈)-alkyl or a 5- or 6-membered monocyclic or 9- or    10-membered bicyclic heterocycle which contains 1, 2, 3 or 4    heteroatoms selected from the group consisting of O, N and S, where    each of the 11 last-mentioned radicals is optionally substituted in    the cyclic moiety by one or more identical or different radicals    R^(bb),

-   R^(aa) independently of one another each represent hydrogen, OH,    (C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,    (C₁-C₈)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₆)-haloalkoxy,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkoxy,    (C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkyl,    (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkynyloxy,    (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkoxy,    —NR*R*, where R* and R** are as defined above,    tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,    tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl,    (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₈)-cycloalkenyl,    (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkenyloxy,    (C₅-C₈)-cycloalkynyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl,    (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl,    phenyl-(C₁-C₈)-alkoxy, phenoxy, phenoxy-(C₁-C₈)-alkyl,    phenoxy-(C₁-C₈)-alkoxy, phenylamino, phenylamino-(C₁-C₈)-alkyl,    phenylamino-(C₁-C₈)-alkoxy or a 5- or 6-membered monocyclic or 9- or    10-membered bicyclic heterocycle which is optionally attached via an    alkylene group or an alkoxy group and contains 1, 2, 3 or 4    heteroatoms selected from the group consisting of O, N and S, where    each of the 20 last-mentioned radicals is optionally substituted in    the cyclic moiety by one or more identical or different radicals    R^(cc), and

-   R^(bb) and R^(cc) independently of one another each represent    halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy or, in the case of saturated or partially    unsaturated cyclic base groups, also represent oxo and

-   M represents an equivalent of a cation, preferably a metal ion    equivalent, an ammonium ion which is optionally substituted by 1 to    4 identical or different radicals from the group consisting of    (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,    (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl, phenyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,    (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, or a    tertiary sulphonium ion which is preferably substituted by 3    identical or different radicals from the group consisting of    (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,    (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl, phenyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,    (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkyl, in    particular (C₁-C₄)-alkyl,    n represents 1, 2, 3, 4 or 5, preferably 1, 2 or 3.

In the formula (I), the formula “(R²)_(n)” means n radicals R² which areattached as substituents at the phenyl ring in question, where theradicals in the case of n greater than 1 may be identical or differentand have the meaning mentioned in each case in more detail.

The compounds of the formula (I) according to the invention include allstereoisomers which can occur on the basis of the centres of asymmetryor double bonds in the molecule whose configuration is not designatedspecifically in the formula or which are not specified explicitly, andmixtures thereof, including the racemic compounds and the mixturesenriched partly with particular stereoisomers. The invention alsoincludes all tautomers, such as keto and enol tautomers, and theirmixtures and salts, if appropriate functional groups are present.

In positions 3 and 4 of the substituted butanoic acid skeleton, thecompounds of the formula (I) contain two centres of chirality, and theytherefore occur in at least four stereoisomers and mixtures thereof,i.e. 2 enantiomeric erythro isomers and 2 enantiomeric threo isomers.Depending on the substituents R¹ and (R²)_(n), one or more furthercentres of chirality may be present.

Accordingly, the invention also provides erythro/threo mixtures(diastereomer mixtures) of the compounds of the formula (I).

The invention also provides the racemic erythro isomers or the racemicthreo isomers of the compounds of the formula (I).

The invention also provides the optically active (3R,4S) and (3S,4R)erythro isomers and mixtures thereof having an excess of one enantiomer.

The invention also provides the optically active (3R,4R) and (3S,4S)threo isomers and mixtures thereof having an excess of one enantiomer.

Owing to the two centres of chirality in positions 3 and 4, compounds ofthe same chemical constitution exist as 4 stereoisomeric configurations,namely two erythro enantiomers having the configurations (3S,4R)[=erythro-1] and (3R,4S) [=erythro-2], respectively, and two threoenantiomers having the configurations (3S,4S) [=threo-1] and (3R,4R)[=threo-2], respectively; see the scheme below:

The compounds (I) according to the invention represent diastereomermixtures of the 4 stereoisomers, but also embrace the separateddiastereomeric erythro or threo forms, in each case as a racemic mixtureof the erythro enantiomers or threo enantiomers or as pure orstereochemically enriched enantiomers erythro-1, erythro-2, threo-1 orthreo-2 mentioned above.

Preference is given to the diastereomer mixtures of the formula (I)(erythro/threo mixtures).

Preference is also given to the racemic erythro mixtures of the formula(I) of the aforementioned enantiomers erythro-1 and erythro-2 in a ratioof 50:50.

Preference is furthermore given to the racemic threo mixtures of theformula (I) of the aforementioned enantiomers threo-1 and threo-2 in aratio of 50:50.

More preference is given to the (3R,4R) enantiomers threo-2 of theformula (Ia) or salts thereof

in which R¹ and (R²)_(n) are as defined in formula (I), where thestereochemical configuration at the carbon atom in position 3 of thebutanoic acid derivative has a stereochemical purity of 60 to 100% (R),preferably 70 to 100% (R), more preferably 80 to 100% (R), in particular90 to 100% (R), based on the mixture of threo enantiomers present, andthe stereochemical configuration at the carbon atom in position 4 of thebutanoic acid derivative has a stereochemical purity of 60 to 100% (R),preferably 70 to 100% (R), more preferably 80 to 100% (R), in particular90 to 100% (R), based on the mixture of threo enantiomers present.

In the case of R¹═H or in the case of suitable acidic substituents, thecompounds of the formula (I) are able to form salts by reaction withbases where the acidic hydrogen is replaced by an agriculturallysuitable cation.

By addition of a suitable inorganic or organic acid onto a basic group,such as, for example, amino or alkylamino or else the nitrogen atom inthe pyridyl ring, the compounds of the formula (I) are able to formsalts. Suitable acidic groups present, such as, for example, carboxylicacid groups, are able to form inner salts with groups which for theirpart can be protonated, such as amino groups.

The compounds of the formula (I) may preferably be present in the formof agriculturally usable salts, where the type of salt is otherwisegenerally immaterial. In general, suitable salts are the salts of thosecations or the acid addition salts of those acids whose cations andanions, respectively, have no adverse effect on the herbicidal activityof the compounds (I).

Suitable cations are in particular ions of the alkali metals, preferablylithium, sodium or potassium, of the alkaline earth metals, preferablycalcium or magnesium, and of the transition metals, preferablymanganese, copper, zinc or iron. The cation used may also be ammonium orsubstituted ammonium, where one to four hydrogen atoms may be replacedhere by (C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,phenyl or benzyl, preferably ammonium, dimethylammonium,diisopropylammonium, tetramethylammonium, tetrabutylammonium,2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium,trimethylbenzylammonium. Also suitable are phosphonium ions, sulphoniumions, preferably tri-(C₁-C₄)-alkylsulphonium, in particulartrimethylsulphonium, or sulphoxonium ions, preferablytri-(C₁-C₄)-alkylsulphoxonium, in particular trimethylsulphoxonium.Anions of useful acid addition salts are primarily chloride, bromide,fluoride, hydrogensulphate, sulphate, dihydrogenphosphate,hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and also the anions of (C₁-C₄)-alkanoicacids, preferably formate, acetate, propionate, butyrate ortrifluoroacetate.

In formula (I) and in all subsequent formulae, chemical radicals arereferred to by names which are collective terms for the enumeration ofindividual group members or specifically refer to individual chemicalradicals. In general, terms are used which are familiar to the personskilled in the art and/or in particular have the meanings illustratedbelow.

A hydrolysable radical (see definition of R¹) is a radical which can behydrolysed under the application conditions, for example a radical whichcan be hydrolysed even in the spray liquor or in particular under thephysiological conditions in plants, where a compound of the formula (I)having the carboxylic ester group —CO—OR¹ (R¹ is not hydrogen) ishydrolysed to the compound of the formula (I) having the carboxylic acidgroup —CO—OH (i.e. the compound (I) where R¹═H). Expressly, thedefinition of the hydrolysable radicals also includes the radicals whereR¹=hydrocarbon radical or heterocyclyl radical, the two last-mentionedradicals being unsubstituted or substituted, even if some of them arehydrolysable comparatively slowly.

A hydrocarbon radical is an aliphatic, cycloaliphatic or aromaticmonocyclic or, in the case of an optionally substituted hydrocarbonradical, also a bicyclic or polycyclic organic radical based on theelements carbon and hydrogen, including, for example, the radicalsalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl,naphthyl, indanyl, indenyl, etc.; this applies correspondingly tohydrocarbon radicals in composite meanings, such as hydrocarbonoxyradicals or other hydrocarbon radicals attached via heteroatom groups.

Unless defined in more detail, the hydrocarbon radicals preferably have1 to 20 carbon atoms, more preferably 1 to 16 carbon atoms, inparticular 1 to 12 carbon atoms. The hydrocarbon radicals, also in thespecial radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino andalkylthio, and also the corresponding unsaturated and/or substitutedradicals may in each case be straight-chain or branched in the carbonskeleton.

The expression “(C₁-C₄)-alkyl” is a brief notation for alkyl having from1 to 4 carbon atoms, i.e. encompasses the methyl, ethyl, 1-propyl,2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals.General alkyl radicals with a larger specified range of carbon atoms,e.g. “(C₁-C₆)-alkyl”, correspondingly also encompass straight-chain orbranched alkyl radicals with a greater number of carbon atoms, i.e.according to the example also the alkyl radicals having 5 and 6 carbonatoms.

Unless stated specifically, preference is given to the lower carbonskeletons, for example having from 1 to 6 carbon atoms, or having from 2to 6 carbon atoms in the case of unsaturated groups, in the case of thehydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals,including in composite radicals. Alkyl radicals, including in thecombined definitions such as alkoxy, haloalkyl, etc., are, for example,methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexylssuch as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such asn-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynylradicals are defined as the possible unsaturated radicals correspondingto the alkyl radicals; alkenyl is, for example, vinyl, allyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl,2-methylpentenyl or hexenyl group, preferably allyl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl.

Alkenyl also includes in particular straight-chain or branchedhydrocarbon radicals having more than one double bond, such as1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenylradicals having one or more cumulated double bonds, for example allenyl(1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.

Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl. Alkynyl also includes, in particular,straight-chain or branched hydrocarbon radicals having more than onetriple bond or else having one or more triple bonds and one or moredouble bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1-yl.

A 3- to 9-membered carbocyclic ring is (C₃-C₉)-cycloalkyl or(C₅-C₉)-cycloalkenyl. (C₃-C₉)-Cycloalkyl is a carbocyclic saturated ringsystem having preferably 3-9 carbon atoms, for example cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl orcyclononyl. In the case of substituted cycloalkyl, cyclic systems withsubstituents are included, where the substituents may also be bonded bya double bond on the cycloalkyl radical, for example an alkylidene groupsuch as methylidene. (C₅-C₉)-Cycloalkenyl is a carbocyclic, nonaromatic,partially unsaturated ring system having 5-9 carbon atoms, for example1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl,3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl,1,3-cyclohexadienyl or 1,4-cyclohexadienyl. In the case of substitutedcycloalkenyl, the explanations for substituted cycloalkyl applycorrespondingly.

Alkylidene, for example also in the form of (C₁-C₁₀)-alkylidene, is theradical of a straight-chain or branched alkane which is bonded via adouble bond, the position of the binding site not being fixed. In thecase of a branched alkane, the only positions possible are, of course,those in which two hydrogen atoms can be replaced by the double bond;radicals are, for example, ═CH₂, ═CH—CH₃, ═C(CH₃)—CH₃, ═C(CH₃)—C₂H₅ or═C(C₂H₅)—C₂H₅.

Halogen is, for example, fluorine, chlorine, bromine or iodine.Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl,respectively, which are partially or fully substituted by identical ordifferent halogen atoms, preferably from the group consisting offluorine, chlorine, bromine and iodine, in particular from the groupconsisting of fluorine, chlorine and bromine, very particularly from thegroup consisting of fluorine and chlorine, for example monohaloalkyl,perhaloalkyl, CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃, CHCl₂, CH₂CH₂Cl;haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ andOCH₂CH₂Cl; this applies correspondingly to haloalkenyl and otherhalogen-substituted radicals such as, for example, halocycloalkyl.

Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl,naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyland the like, preferably phenyl.

Optionally substituted aryl also includes polycyclic systems, such astetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where thepoint of attachment is at the aromatic system.

A heterocyclic radical (heterocyclyl) comprises at least oneheterocyclic ring (=carbocyclic ring in which at least one carbon atomis replaced by a heteroatom, preferably by a heteroatom from the groupconsisting of N, O, S, P, B, Si, Se), which is saturated, unsaturated orheteroaromatic and may be unsubstituted or substituted, where the pointof attachment is located at a ring atom.

Unless defined otherwise, it preferably contains one or more, inparticular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferablyfrom the group consisting of N, O, and S; it is preferably an aliphaticheterocyclyl radical having 3 to 7 ring atoms or a heteroaromaticradical having 5 or 6 ring atoms. The heterocyclic radical may, forexample, be a heteroaromatic radical or ring (heteroaryl), such as, forexample, a monocyclic, bicyclic or polycyclic aromatic system in whichat least 1 ring contains one or more heteroatoms.

If the heterocyclyl radical or the heterocyclic ring is optionallysubstituted, it can be fused to other carbocyclic or heterocyclic rings.Preference is given to benzo-fused heterocyclic or heteroaromatic rings.

Optionally substituted heterocyclyl also includes polycyclic systems,such as, for example, 8-azabicyclo[3.2.1]octanyl or1-azabicyclo[2.2.1]heptyl.

Optionally substituted heterocyclyl also includes spirocyclic systems,such as, for example, 1-oxa-5-azaspiro[2.3]hexyl.

It is preferably a radical of a heteroaromatic ring having a heteroatomfrom the group consisting of N, O and S, for example the radical of afive- or six-membered ring, such as pyridyl, pyrrolyl, thienyl or furyl;

it is furthermore preferably a radical of a corresponding heteroaromaticring having 2, 3 or 4 heteroatoms, for example pyrimidinyl, pyridazinyl,pyrazinyl, triazinyl, tetrazinyl, thiazolyl, thiadiazolyl, oxazolyl,isoxazolyl, pyrazolyl, imidazolyl or triazolyl or tetrazolyl. Here,preference is given to a radical of a heteroaromatic five- orsix-membered ring having 1 to 4 heteroatoms, such as, for example,1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, isothiazolyl,1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, 1,2,3-triazinyl,1,2,4-triazinyl, 1,3,5-triazinyl, 1,2,3,4-tetrazinyl,1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, thiazolyl, isothiazolyl,oxazolyl, isoxazolyl, pyrazolyl, imidazolyl.

More preference is given here to heteroaromatic radicals offive-membered heterocycles having 3 nitrogen atoms, such as1,2,3-triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl,1,2,5-triazol-1-yl, 1,2,5-triazol-3-yl, 1,3,4-triazol-1-yl,1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl;

more preference is also given here to heteroaromatic radicals ofsix-membered heterocycles having 3 nitrogen atoms, such as1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl;more preference is also given here to heteroaromatic radicals offive-membered heterocycles having two nitrogen atoms and one oxygenatom, such as 1,2,4-oxadiazol-3-yl; 1,2,4-oxadiazol-5-yl,1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl,1,2,5-oxadiazol-3-yl,more preference is also given here to heteroaromatic radicals offive-membered heterocycles having two nitrogen atoms and one sulphuratom, such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl,1,2,5-thiadiazol-3-yl;more preference is also given here to heteroaromatic radicals offive-membered heterocycles having four nitrogen atoms, such as1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-5-yl, 1,2,3,5-tetrazol-1-yl,1,2,3,5-tetrazol-4-yl, 2H-1,2,3,4-tetrazol-5-yl,1H-1,2,3,4-tetrazol-5-yl,more preference is also given here to heteroaromatic radicals ofsix-membered heterocycles such as 1,2,4,5-tetrazin-3-yl;more preference is also given here to heteroaromatic radicals offive-membered heterocycles having three nitrogen atoms and one oxygen orsulphur atom, such as 1,2,3,4-oxatriazol-5-yl; 1,2,3,5-oxatriazol-4-yl;1,2,3,4-thiatriazol-5-yl; 1,2,3,5-thiatriazol-4-yl;more preference is also given here to heteroaromatic radicals ofsix-membered heterocycles such as, for example,1,2,4,6-thiatriazin-1-yl; 1,2,4,6-thiatriazin-3-yl;1,2,4,6-thiatriazin-5-yl.

Furthermore preferably, the heterocyclic radical or ring is a partiallyor fully hydrogenated heterocyclic radical having one heteroatom fromthe group of N, O and S, for example oxiranyl, oxetanyl, oxolanyl(=tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.

It is also preferably a partially or fully hydrogenated heterocyclicradical having 2 heteroatoms from the group of N, O and S, for examplepiperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl,isoxazolidinyl and morpholinyl. Suitable substituents for a substitutedheterocyclic radical are the substituents specified later on below, andadditionally also oxo. The oxo group may also occur on the ring heteroatoms which are able to exist in different oxidation states, as in thecase of N and S, for example.

Preferred examples of heterocyclyl are a heterocyclic radical havingfrom 3 to 6 ring atoms from the group of pyridyl, thienyl, furyl,pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (=tetrahydrofuryl),pyrrolidyl, piperidyl, especially oxiranyl, 2-oxetanyl, 3-oxetanyl oroxolanyl, or is a heterocyclic radical having two or three heteroatoms,for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl,thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl,dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl ormorpholinyl.

Preferred heterocyclic radicals are also benzo-fused heteroaromaticrings, for example benzofuryl, benzisofuryl, benzothiophenyl,benzisothiophenyl, isobenzothiophenyl, indolyl, isoindolyl, indazolyl,benzimidazolyl, benzotriazolyl, benzoxazolyl, 1,2-benzisoxazolyl,2,1-benzisoxazolyl, benzothiazolyl, 1,2-benzisothiazolyl,2,1-benzisothiazolyl, 1,2,3-benzoxadiazolyl, 2,1,3-benzoxadiazolyl,1,2,3-benzothiadiazolyl, 2,1,3-benzothiadiazolyl, quinolyl (quinolinyl),isoquinolyl (isoquinolinyl), quinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl,indolizinyl, benzo-1,3-dioxylyl, 4H-benzo-1,3-dioxinyl and4H-benzo-1,4-dioxinyl, and, where possible, N-oxides and salts thereof.When a base structure is substituted “by one or more radicals” from alist of radicals (=group) or a generically defined group of radicals,this in each case includes simultaneous substitution by a plurality ofidentical and/or structurally different radicals. Substituted radicals,such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, phenyl,benzyl, heterocyclyl and heteroaryl radical, are, for example, asubstituted radical derived from the unsubstituted base structure, wherethe substituents are, for example, one or more, preferably 1, 2 or 3,radicals from the group of halogen, alkoxy, alkylthio, hydroxyl, amino,nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl,carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such asacylamino, mono- and dialkylamino, and alkylsulphinyl, alkylsulphonyland, in the case of cyclic radicals, also alkyl, haloalkyl,alkylthioalkyl, alkoxyalkyl, optionally substituted mono- anddialkylaminoalkyl and hydroxyalkyl; in the term “substituted radicals”,such as substituted alkyl, etc., substituents include, in addition tothe saturated hydrocarbon-containing radicals mentioned, correspondingunsaturated aliphatic and aromatic radicals, such as optionallysubstituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy,etc. In the case of substituted cyclic radicals having aliphaticmoieties in the ring, cyclic systems with those substituents which arebonded on the ring by a double bond are also included, for examplesubstituted by an alkylidene group such as methylidene or ethylidene.

The term “radicals from the group consisting of (followed by thegroup=list of the substituents)” is, wherever used, meant to besynonymous with “radicals selected from the group consisting of ( . . .)”. The term “one or more radicals from the group consisting of(followed by the group=list of the substituents)” is, wherever used,meant to be synonymous with “one or more identical or different radicalsselected from the group consisting of ( . . . )”.

The substituents given by way of example (“first substituent level”)can, if they include hydrocarbon-containing fractions, be furthersubstituted therein if desired (“second substituent level”), by forexample one of the substituents as defined for the first substituentlevel. Corresponding further substituent levels are possible. The term“substituted radical” preferably embraces just one or two substituentlevels. “Parent radical” refers to the respective base structure of aradical to which substituents of a substituent level are attached.

Preferred substituents for the substituent levels are, for example,amino, hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carbonamide,SF₅, aminosulphonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl,monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy,alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl,alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio,cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio,alkylsulphinyl, alkylsulphonyl, monoalkylaminosulphonyl,dialkylaminosulphonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl,N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy,benzyl, benzyloxy, benzylthio, arylthio, arylamino and benzylamino. Twosubstituents together may also form a saturated or unsaturatedhydrocarbon bridge or a corresponding bridge in which carbon atoms, CHgroups or CH₂ groups are replaced by heteroatoms, thus forming afused-on or fused cycle. Here, with preference benzo-fused systems basedon the base structure are formed.

Optionally substituted phenyl is preferably phenyl or phenyl which isunsubstituted or substituted by one or more radicals from the groupconsisting of halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio and nitro, inparticular phenyl which is optionally substituted by one or moreradicals from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl and (C₁-C₄)-alkoxy.

In the case of radicals having carbon atoms, preference is given tothose having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms,especially 1 or 2 carbon atoms. Preference is generally given tosubstituents from the group of halogen, e.g. fluorine and chlorine,(C₁-C₄)-alkyl, preferably methyl or ethyl, (C₁-C₄)-haloalkyl, preferablytrifluoromethyl, (C₁-C₄)-alkoxy, preferably methoxy or ethoxy,(C₁-C₄)-haloalkoxy, nitro and cyano. Particular preference is given hereto the substituents methyl, methoxy, fluorine and chlorine.

Substituted amino, such as mono- or disubstituted amino, is a radicalfrom the group of the substituted amino radicals which areN-substituted, for example, by one or two identical or differentradicals from the group of alkyl, alkoxy, acyl and aryl; preferablymono- and dialkylamino, mono- and diarylamino, acylamino,N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; preferenceis given to alkyl radicals having from 1 to 4 carbon atoms; aryl ispreferably phenyl or substituted phenyl; acyl is as defined furtherbelow, preferably (C₁-C₄)-alkanoyl. The same applies to substitutedhydroxylamino or hydrazino.

Acyl is a radical of an organic acid which arises in a formal sense byremoval of a hydroxyl group on the acid function, and the organicradical in the acid may also be bonded to the acid function via aheteroatom. Examples of acyl are the —CO—R radical of a carboxylic acidHO—CO—R and radicals of acids derived therefrom, such as those ofthiocarboxylic acid, optionally N-substituted iminocarboxylic acids orthe radical of carbonic monoesters, N-substituted carbamic acid,sulphonic acids, sulphinic acids, N-substituted sulphonamide acids,phosphonic acids or phosphinic acids.

Acyl is, for example, formyl, alkylcarbonyl such as[(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl,phenyloxycarbonyl, benzyloxycarbonyl, alkylsulphonyl, alkylsulphinyl,N-alkyl-1-iminoalkyl and other radicals of organic acids. The radicalsmay each be substituted further in the alkyl or phenyl moiety, forexample in the alkyl moiety by one or more radicals from the group ofhalogen, alkoxy, phenyl and phenoxy; examples of substituents in thephenyl moiety are the substituents already mentioned above in generalfor substituted phenyl.

Acyl is preferably an acyl radical in the narrower sense, i.e. a radicalof an organic acid in which the acid group is bonded directly to thecarbon atom of an organic radical, for example formyl, alkylcarbonylsuch as acetyl or [(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl,alkylsulphonyl, alkylsulphinyl and other radicals of organic acids. Morepreferably, acyl is an alkanoyl radical having 1 to 6 carbon atoms, inparticular 1 to 4 carbon atoms. Here, (C₁-C₄)-alkanoyl is the radical ofan alkanoic acid having 1 to 4 carbon atoms formed after removal of theOH group of the acid group, i.e. formyl, acetyl, n-propionyl,isopropionyl or n-, i-, sec- or tert-butanoyl.

The “yl position” of a radical denotes the carbon atom having the freebond. Compounds of the formula (I) according to the invention andcompounds of the formula (I) used according to the invention and/orsalts thereof are in short also referred to as “compounds (I)”.

The invention also provides all stereoisomers which are encompassed byformula (I) and mixtures thereof. Such compounds of the formula (I)contain one or more asymmetric carbon atoms or else double bonds whichare not stated separately in the general formulae (I). The possiblestereoisomers defined by their specific three-dimensional shape, such asenantiomers, diastereomers, Z- and E-isomers, are all encompassed by theformula (I) and can be obtained from mixtures of the stereoisomers bycustomary methods or else prepared by stereoselective reactions incombination with the use of stereochemically pure starting materials.

The invention also provides all tautomers of the compounds of theformula (I) which may result from a hydrogen atom shift (for exampleketo-enol tautomers). The compound of the formula (I) also includes thetautomers, even if formally the formula (I) correctly describes only oneof the respective tautomers which are in equilibrium with one another orwhich can be converted into one another.

The compounds of the formula (I) also include all physical forms inwhich they may be present as a pure substance or, if appropriate, as amixture with other compounds, in particular also polymorphic crystalforms of the compounds of the formula (I) or salts thereof or solventadducts (for example hydrates).

Primarily for reasons of higher herbicidal activity, better selectivity,better producibility, better formulatability and/or other relevantproperties, compounds of the abovementioned formula (I) according to theinvention or their salts or their use according to the invention are ofparticular interest in which individual radicals have one of thepreferred meanings already specified or specified below, or inparticular those in which one or more of the preferred meanings alreadyspecified or specified below occur in combination.

Compounds of the formula (I) according to the invention and their usesaccording to the invention with the preferred meanings listed below ofthe symbols or chemical radicals or chemical groups in question are ofparticular interest, irrespective of the respective other radicalsaccording to the symbols R¹ and (R²)_(n) and the definition of n informula (I) and the definitions of the radicals (or chemical groups)according to the symbols R³ to R⁷, Het¹ to Het³, M, R* and R**, R^(A),R^(B), R^(aa), R^(bb) and R^(cc) in the corresponding sub-meanings ofradicals in the formula (I).

Preference is given to the compounds of the formula (I) according to theinvention, preferably of the formula (Ia), or salts thereof in which

-   R¹ represents hydrogen, alkyl, alkenyl or alkynyl, where each of the    3 last-mentioned radicals is unsubstituted or substituted and,    including substituents, has up to 30 carbon atoms, preferably up to    24 carbon atoms, in particular up to 20 carbon atoms, or    -   represents cycloalkyl, cycloalkenyl, cycloalkynyl or aryl, where        each of the 4 last-mentioned radicals is unsubstituted or        substituted and, including substituents, has up to 30 carbon        atoms, preferably up to 24 carbon atoms, in particular up to 20        carbon atoms, or    -   represents a heterocyclyl radical having 3 to 9 ring atoms which        contains 1 to 4 heteroatoms from the group consisting of N, O        and S, which is unsubstituted or substituted and which,        including substituents, has 1 to 30 carbon atoms, preferably 1        to 24 carbon atoms, in particular 1 to 20 carbon atoms.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which R¹ represents hydrogen.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R¹ represents H, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or    (C₂-C₁₈)-alkynyl, where each of the 3 last-mentioned radicals is    unsubstituted or substituted and, including substituents, has up to    30 carbon atoms, preferably up to 24 carbon atoms, in particular up    to 20 carbon atoms, or    -   represents (C₃-C₉)-cycloalkyl, (C₅-C₉)-cycloalkenyl,        (C₅-C₉)-cycloalkynyl or phenyl, where each of the 4        last-mentioned radicals is unsubstituted or substituted and,        including substituents, has up to 30 carbon atoms, preferably up        to 24 carbon atoms, in particular up to 20 carbon atoms.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R¹ represents hydrogen, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or    (C₂-C₁₈)-alkynyl, where each of the 3 last-mentioned radicals is    unsubstituted or substituted by one or more radicals from the group    consisting of the radicals [subgroups (a)-(d)]    -   (a) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy,        (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,        (C₁-C₈)-alkylthio, (C₂-C₈)-alkenylthio, (C₂-C₈)-alkynylthio,        (C₁-C₈)-haloalkylthio, (C₂-C₈)-haloalkenylthio,        (C₂-C₈)-haloalkynylthio, (C_(r) C₈)-alkylsulphinyl,        (C₂-C₈)-alkenylsulphinyl, (C₂-C₈)-alkynylsulphinyl,        (C₁-C₈)-haloalkylsulphinyl, (C₂-C₈)-haloalkenylsulphinyl,        (C₂-C₈)-haloalkynylsulphinyl, (C₁-C₈)-alkylsulphonyl,        (C₂-C₈)-alkenylsulphonyl, (C₂-C₈)-alkynylsulphonyl,        (C₁-C₈)-haloalkylsulphonyl, (C₂-C₈)-haloalkenylsulphonyl,        (C₂-C₈)-haloalkynylsulphonyl, radicals of the formula —NR*R**,        where R* and R** are defined as above or further below, and        -   (C₃-C₈)-cycloalkyl, (C₅-C₈)-cycloalkenyl,            (C₅-C₈)-cycloalkynyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl-S(O)_(p)—,            (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,            (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl-S(O)_(p)—,            (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy,            (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl-S(O)_(p)—,            (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-S(O)_(p)—,            (C₅-C₈)-cycloalkenyloxy, (C₅-C₈)-cycloalkenyl-S(O)_(p)—,            (C₅-C₈)-cycloalkynyloxy, (C₅-C₈)-cycloalkynyl-S(O)_(p)—,            (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkoxy,            (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkyl-S(O)_(p)—, phenyl,            phenyl-(C₁-C₆)-alkoxy, phenoxy, phenyl-S(O)_(p)—,            phenyl-(C₁-C₆)-alkyl-S(O)_(p)—, phenoxy-(C₁-C₆)-alkoxy,            phenoxy-(C₁-C₆)-alkyl-S(O)_(p)—, a radical Het¹,            Het¹-S(O)_(p)—, Het¹-(C₁-C₆)-alkoxy, Het¹-O—,            Het¹-O—(C₁-C₆)-alkoxy, where the heterocyclic radical Het¹            is defined as further above or further below,            -   where each of the 29 last-mentioned radicals is                unsubstituted in the acyclic moiety or substituted by                one or more identical or different radicals R^(A) and is                unsubstituted in the cyclic moiety or substituted by one                or more identical or different radicals R^(B) and p is                in each case independently of the others 0, 1 or 2,        -   and        -   preferably the radicals (a)        -   halogen, cyano, nitro, hydroxy, carboxy, (C₁-C₈)-alkoxy,            (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,            (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,        -   (C₁-C₆)-alkylsulphonyl, (C₁-C₈)-haloalkylsulphonyl,        -   (C₃-C₈)-cycloalkyl,        -   (C₅-C₈)-cycloalkenyl,        -   (C₅-C₈)-cycloalkynyl,        -   (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,        -   (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,        -   (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy,        -   (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkylthio,        -   (C₃-C₈)-cycloalkylsulphinyl, (C₃-C₈)-cycloalkylsulphonyl,        -   (C₃-C₈)-cycloalkoxy-(C₁-C₆)-alkoxy,        -   phenyl, phenoxy, phenylthio, phenylsulphinyl,            phenylsulphonyl,        -   phenyl-(C₁-C₆)-alkoxy, phenyl-(C₁-C₆)-alkylthio,        -   phenyl-(C₁-C₆)-alkylsulphinyl,            phenyl-(C₁-C₆)-alkylsulphonyl,        -   phenoxy-(C₁-C₆)-alkoxy, phenoxy-(C₁-C₆)-alkylthio,            phenoxy-(C₁-C₆)-alkylsulphinyl and            phenoxy-(C₁-C₆)-alkylsulphonyl,            -   where each of the radicals mentioned with cyclic                moieties is unsubstituted in the acyclic moiety or                substituted by one or more identical or different                radicals R^(A) and is unsubstituted in the cyclic moiety                or substituted by one or more identical or different                radicals R^(B),    -   (b) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(C))(R^(D)), —P(═O)(OR^(C))(OR^(D)) and        —O—P(═O)(OR^(C))(OR^(D)), preferably a radical of the formula        —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(C) or        —O—C(═O)—O—R^(C), in particular a radical of the formula        —C(═O)—O—R^(C), —O—C(═O)—R^(C) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined further below,            preferably the radicals (b1)        -   [(C₁-C₈)-alkoxy]carbonyl, [(C₁-C₈)-alkoxy]thiocarbonyl,            [(C₂-C₈)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,            [(C₁-C₈)-alkylthio]carbonyl, [(C₂-C₈)-alkenylthio]carbonyl,            [(C₂-C₈)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,            [(C₂-C₈)-alkenyl]carbonyl, [(C₂-C₈)-alkynyl]carbonyl,            [(C₁-C₈)-alkyl]carbonylamino,            [(C₂-C₈)-alkenyl]carbonylamino,            [(C₂-C₈)-alkynyl]carbonylamino,            [(C₁-C₆)-alkoxy]carbonylamino,            [(C₂-C₈)-alkenyloxy]carbonylamino,            [(C₂-C₈)-alkynyloxy]carbonylamino,            [(C₁-C₈)-alkylamino]carbonylamino,            [(C₁-C₆)-alkyl]carbonyloxy, [(C₂-C₆)-alkenyl]carbonyloxy,            [(C₂-C₆)-alkynyl]carbonyloxy, [(C₁-C₈)-alkoxy]carbonyloxy,            [(C₂-C₈)-alkenyloxy]carbonyloxy and            [(C₂-C₈)-alkynyloxy]carbonyloxy, where each of the 23            last-mentioned radicals is unsubstituted or substituted by            one or more radicals from the group consisting of halogen,            NO₂, (C₁-C₄)-alkoxy and optionally halogen-, CN—, NO₂—,            (C₁-C₄)-alkyl-, (C₁-C₄)-alkoxy- and            (C₁-C₄)-alkylthio-substituted phenyl, and preferably the            radicals (b2)        -   (C₃-C₈)-cycloalkylcarbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkoxycarbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkylcarbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₆-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₆-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₆-C₈)-cycloalkenyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₆-C₈)-cycloalkynyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkoxycarbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkylcarbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₆-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonylamino,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₈)-alkyl]carbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₈)-alkoxy]carbonylamino,        -   (C₃-C₈)-cycloalkoxycarbonylamino,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₈)-alkyl]carbonylamino and        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₈)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₈)-alkyl]carbonyl,        -   phenyl-[(C₁-C₈)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₆)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₈)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₈)-alkyl]carbonyloxy,        -   phenyl-[(C₁-C₈)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₈)-alkyl]carbonyloxy,        -   phenoxy-[(C₁-C₈)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₈)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₈)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₈)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₈)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and is unsubstituted            at the ring or at the polycyclic system or substituted by            one or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₈)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OH)₂, in which each of the        radicals R′ independently of the others represents H,        (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted        by one or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy and nitro or is substituted at two adjacent        positions by a (C₂-C₆)-alkylene bridge, and q represents an        integer from 0 to 6, and    -   (d) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in        which each of the radicals R″ independently of the others        represents H or (C₁-C₄)-alkyl or together the radicals represent        a (C₁-C₆)-alkylene group and R″′ represents H or (C₁-C₄)-alkyl,    -   or-   R¹ represents (C₃-C₉)-cycloalkyl, (C₅-C₉)-cycloalkenyl,    (C₅-C₉)-cycloalkynyl or phenyl,    -   where each of the 4 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        the radicals [subgroups (a′)-(e′)]    -   (a′) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl, (C₂-C₈)-alkynyl,        (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy, (C₂-C₈)-alkenyloxy,        (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₈)-alkylthio,        (C₂-C₈)-alkenylthio, (C₂-C₈)-alkynylthio and radicals of the        formulae —NR*R**, where the radicals R* and R** are defined        further below,    -   (b′) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(C))(R^(D)), —P(═O)(OR^(C))(OR^(D)) and        —O—P(═O)(OR^(C))(OR^(D)), preferably a radical of the formula        —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(C) or        —O—C(═O)—O—R^(C), in particular a radical of the formula        —C(═O)—O—R^(C), —O—C(═O)—R^(C) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined further below,            and preferably the radicals (b1′)        -   [(C₁-C₈)-alkoxy]carbonyl, [(C₁-C₈)-alkoxy]thiocarbonyl,            [(C₂-C₈)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,            [(C₁-C₈)-alkylthio]carbonyl, [(C₂-C₈)-alkenylthio]carbonyl,            [(C₂-C₈)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,            [(C₂-C₈)-alkenyl]carbonyl, [(C₂-C₈)-alkynyl]carbonyl,            (C₁-C₄)-alkylimino, (C₁-C₄)-alkoxyimino,            [(C₁-C₈)-alkyl]carbonylamino,            [(C₂-C₈)-alkenyl]carbonylamino,            [(C₂-C₈)-alkynyl]carbonylamino,            [(C₁-C₈)-alkoxy]carbonylamino,            [(C₂-C₈)-alkenyloxy]carbonylamino,            [(C₂-C₈)-alkynyloxy]carbonylamino,            [(C₁-C₈)-alkylamino]carbonylamino,            [(C₁-C₆)-alkyl]carbonyloxy, [(C₂-C₆)-alkenyl]carbonyloxy,            [(C₂-C₆)-alkynyl]carbonyloxy, [(C₁-C₈)-alkoxy]carbonyloxy,            [(C₂-C₈)-alkenyloxy]carbonyloxy,            [(C₂-C₈)-alkynyloxy]carbonyloxy, (C₁-C₈)-alkylsulphinyl and            (C₁-C₈)-alkylsulphonyl, where each of the 27 last-mentioned            radicals is unsubstituted or substituted by one or more            radicals from the group consisting of halogen, NO₂,            (C₁-C₄)-alkoxy and optionally substituted phenyl, and            preferably the radicals (b2′)        -   (C₃-C₈)-cycloalkylcarbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkoxycarbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyl,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyl,        -   (C₃-C₈)-cycloalkylcarbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₆-C₈)-cycloalkenyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₆-C₈)-cycloalkynyl-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₆-C₈)-cycloalkenyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₆-C₈)-cycloalkynyl-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkoxycarbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkyl]carbonyloxy,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₆)-alkoxy]carbonyloxy,        -   (C₃-C₈)-cycloalkylcarbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₈)-alkyl]carbonylamino,        -   (C₅-C₈)-cycloalkenyl-[(C₁-C₈)-alkyl]carbonylamino,        -   (C₅-C₈)-cycloalkynyl-[(C₁-C₈)-alkyl]carbonylamino,        -   (C₃-C₈)-cycloalkyl-[(C₁-C₈)-alkoxy]carbonylamino,        -   (C₃-C₈)-cycloalkoxycarbonylamino,        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₈)-alkyl]carbonylamino and        -   (C₃-C₈)-cycloalkoxy-[(C₁-C₈)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₈)-alkyl]carbonyl,        -   phenyl-[(C₁-C₆)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₈)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₈)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₈)-alkyl]carbonyloxy,        -   phenyl-[(C₁-C₈)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₈)-alkyl]carbonyloxy,        -   phenoxy-[(C₁-C₈)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₈)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₈)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₈)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₈)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and is unsubstituted            at the ring or at the polycyclic system or substituted by            one or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OR′)₂, in which each of the        radicals R′ independently of the others represents H,        (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted        by one or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy and nitro or is substituted at two adjacent        positions by a (C₂-C₆)-alkylene bridge, and q represents an        integer from 0 to 6, and    -   (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in        which each of the radicals R″ independently of the others is H        or (C₁-C₄)-alkyl or together the radicals are a (C₁-C₆)-alkylene        group and R″′ is H or (C₁-C₄)-alkyl, and    -   (e′) a radical of the formula Het′ which is unsubstituted or        substituted by one or more identical or different radicals        R^(B),    -   or-   R¹ represents a polycyclic radical based on (C₃-C₉)-cycloalkyl,    (C₅-C₉)-cycloalkenyl, (C₅-C₉)-cycloalkynyl or phenyl, where the base    ring is fused with a carbocyclic or heterocyclic ring, preferably a    5- or 6-membered ring having 0 or 1 to 3 ring heteroatoms from the    group consisting of N, O and S, preferably benzo-fused, and where    the base ring or the polycyclic system is unsubstituted or    substituted by one or more identical or different radicals R^(B),    preferably unsubstituted or substituted by one or more radicals from    the group consisting of halogen, cyano, nitro, hydroxy, carboxy,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy,    (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-alkylthio,    (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,    [(C₁-C₆)-haloalkoxy]carbonyl and oxo, or-   R¹ represents a heterocyclic radical Het′ which is unsubstituted at    the ring or at the polycyclic system or substituted by one or more    identical or different radicals R^(B), preferably unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, cyano, thio, nitro, hydroxy, carboxy, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,    (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,    (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkox_(Y),    [(C₁-C₈)-alkoxy]carbonyl, [(C₁-C₆)-haloalkoxy]carbonyl and oxo,    where in the radicals mentioned above and in the radicals below-   Het¹ in each case independently of the others is a saturated,    partially unsaturated or heteroaromatic monocyclic heterocyclyl    radical having 3 to 9 ring atoms, preferably having 5 or 6 ring    atoms, or a 9- or 10-membered bicyclic heterocycle which contains 1,    2, 3 or 4 heteroatoms selected from the group consisting of 0, N and    S, preferably a 5- or 6-membered heterocycle having 1 to 3 ring    heteroatoms from the group consisting of N, O and S which is    optionally also fused to a carbocyclic or heterocyclic ring,    preferably a carbocyclic ring having 3 to 6 carbon atoms or a    heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring    heteroatoms from the group consisting of N, O and S, preferably    optionally benzo-fused,-   R*, R** independently of one another (i.e. also of other groups    NR*R**) each represent H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl,    (C₂-C₈)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,    [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl,    where each of the 4 last-mentioned radicals is optionally    substituted in the cycle by one or more identical or different    radicals R^(bb), or-   R* and R** together with the nitrogen atom represent a 3- to    8-membered heterocycle which, in addition to the nitrogen atom, may    contain one or two further ring heteroatoms from the group    consisting of N, O and S and which is unsubstituted or substituted    by one or more radicals from the group consisting of (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl and oxo,-   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,-   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₆)-alkyl,    (C₁-C₄)-haloalkyl, cyano-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,    nitro-(C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy,    (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkoxy,    (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,    (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,    (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of the    formula R^(aa)—C(═O)— or R^(aa)—C(═O)—(C₁-C₆)-alkyl, the radicals    R^(aa) being defined further below, —NR*R**, R* and R** being    defined further below, tri-[(C₁-C₄)-alkyl]silyl,    tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkoxy, phenyl, phenyl-(C₁-C₆)-alkyl,    phenoxy, phenoxy-(C₁-C₆)-alkyl, phenylamino,    phenylamino-(C₁-C₆)-alkyl or a 5- or 6-membered monocyclic or 9- or    10-membered bicyclic heterocycle which contains 1, 2, 3 or 4    heteroatoms selected from the group consisting of O, N and S, where    each of the 11 last-mentioned radicals is optionally substituted in    the cyclic moiety by one or more identical or different radicals    R^(bb),-   R^(C), R^(D) are each independently of one another (also    independently of radicals R^(C), R^(D) in other groups)    -   hydrogen, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or (C₂-C₈)-alkynyl,        -   where each of the 3 last-mentioned radicals is unsubstituted            or substituted by one or more radicals from the group            consisting of halogen, cyano, nitro, hydroxy,            (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,            (C₁-C₈)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₈)-alkylthio, (C₁-C₈)-haloalkylthio,            (C₁-C₈)-alkylsulphinyl, (C₁-C₈)-haloalkylsulphinyl,            (C₁-C₈)-alkylsulphonyl, (C₁-C₈)-haloalkylsulphonyl and            tri-[(C₁-C₄)-alkyl]silyl,    -   or    -   (C₃-C₈)-cycloalkyl, (C₅-C₈)-cycloalkenyl, (C₅-C₈)-cycloalkynyl,        phenyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl, phenyl-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkyloxy-(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkyl-S(O)_(p)—(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkenyloxy-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkynyloxy-(C₁-C₆)-alkyl, phenoxy-(C₁-C₆)-alkyl,        phenyl-S(O)_(p)—(C₁-C₆)-alkyl,        (C₃-C₈)-cycloalkylamino-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkenylamino-(C₁-C₆)-alkyl,        (C₅-C₈)-cycloalkynylamino-(C₁-C₆)-alkyl,        phenylamino-(C₁-C₆)-alkyl, Het¹, Het¹-(C₁-C₆)-alkyl,        Het¹-O—(C₁-C₆)-alkyl or Het¹-S(O)_(p)—(C₁-C₆)-alkyl, where Het¹        has the meaning mentioned,        -   where each of the 22 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B) and p            independently of the others in each case represents 0, 1 or            2,-   R^(aa) independently of one another each represent hydrogen, OH,    (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₆)-alkoxy,    (C₃-C₆)-alkenyloxy, (C₃-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₃-C₆)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₆)-alkynyloxy,    (C₃-C₆)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₆)-alkynyloxy-(C₁-C₆)-alkoxy,    —NR*R*, where R* and R** are as defined above,    tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,    tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₆)-cycloalkenyl,    (C₅-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₆)-cycloalkenyloxy,    (C₅-C₆)-cycloalkynyl, (C₅-C₆)-cycloalkynyl-(C₁-C₆)-alkyl,    (C₅-C₆)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₆)-alkyl,    phenyl-(C₁-C₆)-alkoxy, phenoxy, phenoxy-(C₁-C₆)-alkyl,    phenoxy-(C₁-C₆)-alkoxy, phenylthio, phenyl-S(O)_(p)—(C₁-C₆)-alkyl,    phenyl-S(O)_(p)—(C₁-C₆)-alkoxy, where p independently of the others    in each case represents 0, 1 or 2, phenylamino,    phenylamino-(C₁-C₆)-alkyl, phenylamino-(C₁-C₆)-alkoxy or a 5- or    6-membered monocyclic or 9- or 10-membered bicyclic heterocycle    which is optionally attached via an alkylene group or an alkoxy    group and contains 1, 2, 3 or 4 heteroatoms selected from the group    consisting of O, N and S, where each of the 20 last-mentioned    radicals is optionally substituted in the cyclic moiety by one or    more identical or different radicals R^(cc), and-   R^(bb) and R^(cc) independently of one another each represent    halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R¹ represents hydrogen, (C₁-C₁₈)-alkyl, (C₂-C₁₈)-alkenyl or    (C₂-C₁₈)-alkynyl, preferably H, (C₁-C₁₂)-alkyl, (C₂-C₁₂)-alkenyl or    (C₂-C₁₂)-alkynyl, in particular H, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl or    (C₂-C₈)-alkynyl, more preferably H or (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl    or (C₂-C₆)-alkynyl, more preferably (C₁-C₄)-alkyl, where each of the    13 last-mentioned radicals containing carbon atoms is unsubstituted    or substituted by one or more radicals from the group consisting of    the radicals [subgroups (a)-(d)]    -   (a) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,        (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,        (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,        (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio,        (C₂-C₆)-haloalkynylthio, (C₁-C₆)-alkylsulphinyl,        (C₂-C₆)-alkenylsulphinyl, (C₂-C₆)-alkynylsulphinyl,        (C₁-C₆)-haloalkylsulphinyl, (C₂-C₆)-haloalkenylsulphinyl,        (C₂-C₆)-haloalkynylsulphinyl, (C₁-C₆)-alkylsulphonyl,        (C₂-C₆)-alkenylsulphonyl, (C₂-C₆)-alkynylsulphonyl,        (C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenylsulphonyl,        (C₂-C₆)-haloalkynylsulphonyl, radicals of the formula —NR*R**,        where R* and R** are defined further below, and        (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,        (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy,        (C₅-C₆)-cycloalkenyl-(C₁-C₄)-alkoxy,        (C₅-C₆)-cycloalkynyl-(C₁-C₄)-alkoxy, (C₃-C₆)-cycloalkoxy,        (C₅-C₆)-cycloalkenyloxy, (C₅-C₆)-cycloalkynyloxy,        (C₃-C₆)-cycloalkoxy-(C₁-C₄)-alkoxy, phenyl,        phenyl-(C₁-C₆)-alkoxy, phenoxy, phenoxy-(C₁-C₄)-alkoxy,        phenyl-S(O)_(p)—, phenyl-(C₁-C₆)-alkyl-S(O)_(p)—,        phenyloxy-(C₁-C₆)-alkyl-S(O)_(p)—, a radical Het¹,        Het¹-(C₁-C₆)-alkoxy, Het¹-O—, Het¹-O—(C₁-C₄)-alkoxy,        Het¹-(C₁-C₆)-alkoxy, Het¹-S(O)_(p)—,        Het¹-O—(C₁-C₄)-alkyl-S(O)_(p)—, where the heterocyclic radical        Het¹ is defined as further above or below,        -   where each of the 24 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B) and p            independently of the others in each case represents 0, 1 or            2,    -   and    -   preferably the radicals (a1)    -   halogen, cyano, nitro, hydroxy, carboxy, (C₁-C₆)-alkoxy,        (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,        (C₁-C₆)-alkylthio, (C₁-C₆)-haloalkylthio,        (C₁-C₆)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl,        (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,        (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkoxy,        (C₅-C₄)-cycloalkenyl-(C₁-C₄)-alkoxy,        (C₅-C₄)-cycloalkynyl-(C₁-C₄)-alkoxy, (C₃-C₄)-cycloalkoxy,        (C₃-C₄)-cycloalkoxy-(C₁-C₄)-alkoxy, phenyl,        phenyl-(C₁-C₄)-alkoxy, phenoxy and phenoxy-(C₁-C₄)-alkoxy,        phenylthio, phenylsulphinyl, phenylsulphonyl,        -   where each of the radicals (a1) is unsubstituted in the            acyclic moiety or substituted by one or more identical or            different radicals R^(A) and is unsubstituted in the cyclic            moiety or substituted by one or more identical or different            radicals R^(B),    -   (b) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(C))(R^(D)), —P(═O)(OR^(C))(OR^(D)) and        —O—P(═O)(OR^(C))(OR^(D)), preferably a radical of the formula        —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(C) or        —O—C(═O)—O—R^(C), in particular a radical of the formula        —C(═O)—O—R^(C), —O—C(═O)—R^(C) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined further below,        -   preferably the radicals (b1)        -   [(C₁-C₆)-alkoxy]carbonyl, [(C₁-C₆)-alkoxy]thiocarbonyl,            [(C₂-C₆)-alkenyloxy]carbonyl, [(C₂-C₈)-alkynyloxy]carbonyl,            [(C₁-C₆)-alkylthio]carbonyl, [(C₂-C₆)-alkenylthio]carbonyl,            [(C₂-C₆)-alkynylthio]carbonyl, (C₁-C₆)-alkanoyl,            [(C₂-C₆)-alkenyl]carbonyl, [(C₂-C₆)-alkynyl]carbonyl,            [(C₁-C₆)-alkyl]carbonylamino,            [(C₂-C₆)-alkenyl]carbonylamino,            [(C₂-C₆)-alkynyl]carbonylamino,            [(C₁-C₆)-alkoxy]carbonylamino,            [(C₂-C₆)-alkenyloxy]carbonylamino,            [(C₂-C₆)-alkynyloxy]carbonylamino,            [(C₁-C₆)-alkylamino]carbonylamino,            [(C₁-C₆)-alkyl]carbonyloxy, [(C₂-C₆)-alkenyl]carbonyloxy,            [(C₂-C₆)-alkynyl]carbonyloxy, [(C₁-C₆)-alkoxy]carbonyloxy,            [(C₂-C₆)-alkenyloxy]carbonyloxy and            [(C₂-C₆)-alkynyloxy]carbonyloxy, where each of the 23            last-mentioned radicals is unsubstituted or substituted by            one or more radicals from the group consisting of halogen,            NO₂, (C₁-C₄)-alkoxy and optionally halogen-, CN—, NO₂—,            (C₁-C₄)-alkyl-, (C₁-C₄)-alkoxy- and            (C₁-C₄)-alkylthio-substituted phenyl, and        -   preferably the radicals (b2)        -   (C₃-C₆)-cycloalkylcarbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkoxycarbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkylcarbonyloxy,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkoxycarbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkylcarbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₅-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₅-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   (C₃-C₆)-cycloalkoxycarbonylamino,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonylamino and        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₄)-alkyl]carbonyl,        -   phenyl-[(C₁-C₄)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₄)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₄)-alkyl]carbonylox_(Y),        -   phenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₄)-alkyl]carbonylox_(Y),        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₄)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and is unsubstituted            at the ring or at the polycyclic system or substituted by            one or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₄)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OR)₂, in which each of the        radicals R′ independently of the others represents H,        (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted        by one or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy and nitro or is substituted at two adjacent        positions by a (C₂-C₆)-alkylene bridge, and q represents an        integer from 0 to 6, and    -   (d) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in        which each of the radicals R″ independently of the others        represents H or (C₁-C₄)-alkyl or together the radicals represent        a (C₁-C₆)-alkylene group and R″′ represents H or (C₁-C₄)-alkyl,    -   or-   R¹ represents (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl,    (C₅-C₆)-cycloalkynyl or phenyl,    -   where each of the 4 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        the radicals [subgroups (a′)-(e′)]    -   (a′) halogen, cyano, thio, nitro, hydroxy, carboxy,        (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl,        (C₂-C₆)-haloalkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy,        (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkoxy,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₆)-alkylthio,        (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio and radicals of the        formulae —NR*R**, where the radicals R* and R** are as defined        above or further below,    -   (b′) radicals of the formulae —C(═O)—R^(C), —C(═O)—O—R^(C),        —O—C(═O)—R^(C), —O—C(═O)—O—R^(C), —C(═O)—S—R^(C),        —C(═S)—S—R^(C), —C(═S)—S—R^(C), —C(═O)—NR*R**, —C(═O)—O—NR*R**,        —O—C(═O)—NR*R**, —N(R*)—C(═O)—R^(C), —N(R*)—C(═O)—NR*R**,        —N(R*)—C(═O)—O—R^(C), —P(═O)(R^(C))(R^(D)),        —P(═O)(OR^(C))(R^(D)), —P(═O)(OR^(C))(OR^(D)) and        —O—P(═O)(OR^(C))(OR^(D)), preferably a radical of the formula        —C(═O)—R^(C), —C(═O)—O—R^(C), —O—C(═O)—R^(C) or        —O—C(═O)—O—R^(C), in particular a radical of the formula        —C(═O)—O—R^(C), —O—C(═O)—R^(C) or —O—C(═O)—O—R^(C),        -   where R*, R**, R^(C) and R^(D) are as defined further below,        -   and preferably the radicals (b1′)        -   [(C₁-C₆)-alkoxy]carbonyl, [(C₁-C₆)-alkoxy]thiocarbonyl,            [(C₂-C₆)-alkenyloxy]carbonyl, [(C₂-C₆)-alkynyloxy]carbonyl,            [(C₁-C₆)-alkylthio]carbonyl, [(C₂-C₆)-alkenylthio]carbonyl,            [(C₂-C₆)-alkynylthio]carbonyl, (C₁-C₈)-alkanoyl,            [(C₂-C₆)-alkenyl]carbonyl, [(C₂-C₆)-alkynyl]carbonyl,            (C₁-C₄)-alkylimino, (C₁-C₄)-alkoxyimino,            [(C₁-C₆)-alkyl]carbonylamino,            [(C₂-C₆)-alkenyl]carbonylamino,            [(C₂-C₆)-alkynyl]carbonylamino,            [(C₁-C₆)-alkoxy]carbonylamino,            [(C₂-C₆)-alkenyloxy]carbonylamino,            [(C₂-C₆)-alkynyloxy]carbonylamino,            [(C₁-C₆)-alkylamino]carbonylamino,            [(C₁-C₄)-alkyl]carbonyloxy, [(C₂-C₄)-alkenyl]carbonyloxy,            [(C₂-C₄)-alkynyl]carbonyloxy, [(C₁-C₆)-alkoxy]carbonyloxy,            [(C₂-C₆)-alkenyloxy]carbonyloxy,            [(C₂-C₆)-alkynyloxy]carbonyloxy, (C₁-C₆)-alkylsulphinyl and            (C₁-C₆)-alkylsulphonyl, where each of the 27 last-mentioned            radicals is unsubstituted or substituted by one or more            radicals from the group consisting of halogen, NO₂,            (C₁-C₄)-alkoxy and optionally substituted phenyl, and            preferably the radicals (b2′)        -   (C₃-C₆)-cycloalkylcarbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkoxycarbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyl,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   (C₃-C₆)-cycloalkylcarbonyloxy,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₆-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₆-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₆-C₆)-cycloalkenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₆-C₆)-cycloalkynyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkoxycarbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonyloxy,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   (C₃-C₆)-cycloalkylcarbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₆-C₆)-cycloalkenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₆-C₆)-cycloalkynyl-[(C₁-C₄)-alkyl]carbonylamino,        -   (C₃-C₆)-cycloalkyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   (C₃-C₆)-cycloalkoxycarbonylamino,        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkyl]carbonylamino and        -   (C₃-C₆)-cycloalkoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenylcarbonyl,        -   phenyl-[(C₁-C₄)-alkyl]carbonyl,        -   phenyl-[(C₁-C₄)-alkoxy]carbonyl,        -   phenoxycarbonyl,        -   phenoxy-[(C₁-C₄)-alkyl]carbonyl,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyl,        -   phenylcarbonyloxy,        -   phenyl-[(C₁-C₄)-alkyl]carbonyloxy,        -   phenyl-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenoxycarbonyloxy,        -   phenoxy-[(C₁-C₄)-alkyl]carbonyloxy,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonyloxy,        -   phenylcarbonylamino,        -   phenyl-[(C₁-C₄)-alkyl]carbonylamino,        -   phenyl-[(C₁-C₄)-alkoxy]carbonylamino,        -   phenoxycarbonylamino,        -   phenoxy-[(C₁-C₄)-alkyl]carbonylamino,        -   phenoxy-[(C₁-C₄)-alkoxy]carbonylamino,        -   where each of the 42 last-mentioned radicals is optionally            fused in the cyclic moiety with a carbocyclic or            heterocyclic ring, preferably a carbocyclic ring having 3 to            6 carbon atoms or a heterocyclic ring having 5 or 6 ring            atoms and 1 to 3 ring heteroatoms from the group consisting            of N, O and S, preferably benzo-fused, and is unsubstituted            at the ring or at the polycyclic system or substituted by            one or more radicals from the group consisting of halogen,            (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,            (C₁-C₄)-haloalkoxy and nitro, and    -   (c′) radicals of the formulae —SiR′₃, —O—SiR′₃,        (R′)₃Si—(C₁-C₆)-alkoxy, —CO—O—NR′₂, —O—N═CR′₂, —N═CR′₂, —O—NR′₂,        —CH(OR′)₂ and —O—(CH₂)_(q)—CH(OH)₂, in which each of the        radicals R′ independently of the others represents H,        (C₁-C₄)-alkyl or phenyl, which is unsubstituted or substituted        by one or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy and nitro or is substituted at two adjacent        positions by a (C₂-C₆)-alkylene bridge, and q represents an        integer from 0 to 6, and    -   (d′) radicals of the formula R″O—CHR′″CH(OR″)—(C₁-C₆)-alkoxy, in        which each of the radicals R″ independently of the others is H        or (C₁-C₄)-alkyl or together the radicals are a (C₁-C₆)-alkylene        group and R″′ is H or (C₁-C₄)-alkyl, and    -   (e′) a radical of the formula Het¹ which is unsubstituted or        substituted by one or more identical or different radicals        R^(B),    -   or-   R¹ represents a polycyclic radical based on (C₃-C₆)-cycloalkyl,    (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl or phenyl, where the base    ring is fused with a carbocyclic or heterocyclic ring, preferably a    5- or 6-membered ring having 0 or 1 to 3 ring heteroatoms from the    group consisting of N, O and S, preferably benzo-fused, and where    the base ring or the polycyclic system is unsubstituted or    substituted by one or more identical or different radicals R^(B),    preferably unsubstituted or substituted by one or more radicals from    the group consisting of halogen, cyano, nitro, hydroxy, carboxy,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-haloalkynyl, (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy,    (C₂-C₄)-alkynyloxy, (C_(r) C₄)-haloalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,    (C₂-C₄)-alkenylthio, (C₂-C₄)-alkynylthio, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₄)-haloalkoxy]carbonyl and oxo,    -   or-   R¹ represents a heterocyclic radical Het¹ which is unsubstituted at    the ring or at the polycyclic system or substituted by one or more    identical or different radicals R^(B), preferably unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, cyano, thio, nitro, hydroxy, carboxy, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₆)-haloalkynyl,    (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₄)-alkylthio, (C₂-C₄)-alkenylthio, (C₂-C₄)-alkynylthio,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₄)-haloalkoxy]carbonyl and oxo,    where Het¹, R*, R**, R^(A), R^(B), R^(C), R^(D), R^(aa), R^(bb) and    R^(cc) have the meanings already mentioned above, preferably-   Het¹ in each case independently of the others is a saturated,    partially unsaturated or heteroaromatic monocyclic heterocyclyl    radical having 3 to 9 ring atoms, preferably having 5 or 6 ring    atoms, or a 9- or 10-membered bicyclic heterocycle which contains 1,    2, 3 or 4 heteroatoms selected from the group consisting of O, N and    S, preferably a 5- or 6-membered heterocycle having 1 to 3 ring    heteroatoms from the group consisting of N, O and S which is    optionally also fused to a carbocyclic or heterocyclic ring,    preferably a carbocyclic ring having 3 to 6 carbon atoms or a    heterocyclic ring having 5 or 6 ring atoms and 1 to 3 ring    heteroatoms from the group consisting of N, O and S, preferably    optionally benzo-fused,-   R*, R** independently of one another (i.e. also of other groups    NR*R**) each represent H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,    [(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,    [(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl, phenyl, phenyl-(C₁-C₄)-alkyl,    where each of the 4 last-mentioned radicals is optionally    substituted in the cycle by one or more identical or different    radicals R^(bb), or preferably    -   H, (C₁-C₄)-alkyl, allyl, propargyl,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, formyl, acetyl, n-propanoyl,        isopropanoyl, trifluoroacetyl, trichloroacetyl, methoxycarbonyl,        ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, sec-,        t-butoxycarbonyl, [(C₁-C₄)-haloalkoxy]carbonyl, cyclopropyl,        cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, phenyl,        benzyl, 1- or 2-phenylethyl,-   R* and R** together with the nitrogen atom represent a preferably    saturated 5- to 6-membered heterocycle which, in addition to the    nitrogen atom, may contain one or two further ring heteroatoms from    the group consisting of N, O and S and which is unsubstituted or    substituted by one or more radicals from the group consisting of    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo, preferably a 1-piperidine,    1-piperazine, 1-pyrrolidine, 1-pyrazolidine, 1-piperazolidine or    1-morpholine radical,-   R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,-   R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, cyano-(C₁-C₄)-alkyl, hydroxy-(C₁-C₄)-alkyl,    nitro-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,    (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkylsulphonyl, a radical of the    formula R″—C(═O)— or R″—C(═O)—(C₁-C₆)-alkyl, where the radicals R″    are defined further below, —NR*R**, where R* and R** are defined    further below, cyclopropyl, cyclopropylmethyl, phenyl, benzyl, 1- or    2-phenylethyl, phenoxy, 2-phenoxyethyl or a 5- or 6-membered    monocyclic or 9- or 10-membered bicyclic heterocycle which contains    1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N    and S, where each of the 9 last-mentioned radicals is optionally    substituted in the cyclic moiety by one or more identical or    different radicals R^(bb),-   R^(C), R^(D) are each independently of one another (also    independently of radicals R^(C), R^(D) in other groups)    -   hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,        -   where each of the 3 last-mentioned radicals is unsubstituted            or substituted by one or more radicals from the group            consisting of halogen, cyano, nitro, hydroxy,            (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₄)-alkynyloxy,            (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,            (C₁-C₄)-alkylthio, (C₁-C₆)-alkylsulphonyl and            (C₁-C₆)-haloalkylsulphonyl,    -   or    -   (C₃-C₆)-cycloalkyl, (C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkynyl,        phenyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, phenyl-(C₁-C₄)-alkyl,        phenoxy-(C₁-C₄)-alkyl or phenylamino-(C₁-C₆)-alkyl, radicals        Het¹, Het¹-(C₁-C₆)-alkyl, Het¹-O—(C₁-C₆)-alkyl, where Het¹ has        the meaning mentioned,        -   where each of the 12 last-mentioned radicals is            unsubstituted in the acyclic moiety or substituted by one or            more identical or different radicals R^(A) and is            unsubstituted in the cyclic moiety or substituted by one or            more identical or different radicals R^(B),-   R^(aa) independently of one another each represent hydrogen, OH,    (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,    (C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyloxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkoxy,    —NR*R*, where R* and R** are as defined above, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkoxy, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl,    (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₄)-alkyl,    phenyl-(C₁-C₄)-alkoxy, phenoxy, phenoxy-(C₁-C₄)-alkyl,    phenoxy-(C₁-C₄)-alkoxy, phenylamino, phenylamino-(C₁-C₄)-alkyl,    phenylamino-(C₁-C₄)-alkoxy or a 5- or 6-membered monocyclic or 9- or    10-membered bicyclic heterocycle which is optionally attached via a    (C₁-C₄)-alkylene group or a (C₁-C₄)-alkoxy group and contains 1, 2,    3 or 4 heteroatoms selected from the group consisting of O, N and S,    where each of the 14 last-mentioned radicals is optionally    substituted in the cyclic moiety by one or more identical or    different radicals R^(cc),-   R^(bb) independently of one another each represent halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy, preferably halogen, methyl, CF₃, CCl₃, methoxy,    ethoxy, OCH₂F, OCF₂H or OCF₃ and-   R^(cc) independently of one another each represent halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or    (C₁-C₄)-haloalkoxy, preferably halogen, methyl, CF₃, CCl₃, methoxy,    ethoxy, OCH₂F, OCF₂H or OCF₃.

More preference is here also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R¹ represents H, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    -   where each of the 3 last-mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, alkylsulphinyl,        alkylsulphonyl, (C₃-C₆)-cycloalkyl which is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen and (C₁-C₄)-alkyl, and phenyl, phenoxy, phenylthio,        phenylsulphinyl, phenylsulphonyl, where the phenyl ring in the 5        last-mentioned radicals is in each case unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl,        and a radical Het¹, preferably a saturated or partially        unsaturated monocyclic heterocyclyl radical which has 5 or 6        ring atoms and contains 1, 2 or 3 heteroatoms selected from the        group consisting of O, N and S and is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl,    -   or-   R¹ represents (C₃-C₆)-cycloalkyl which is unsubstituted or    substituted by one or more radicals from the group consisting of    (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C_(r) C₄)-haloalkyl,    -   or-   R¹ represents phenyl which is unsubstituted or substituted by one or    more radicals from the group consisting of halogen, (C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl.

Particular preference is here also given to compounds (I), preferably ofthe formula (Ia), or salts thereof in which

-   R¹ represents H, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or (C₂-C₄)-alkynyl,    where each of the 3 last-mentioned radicals is unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, cyclopropyl, cyclobutyl,    where each of the two last-mentioned radicals is unsubstituted or    substituted by one or more radicals from the group consisting of    halogen and (C₁-C₄)-alkyl, and phenyl, phenylthio    (=phenylsulphanyl), phenylsulphinyl, phenylsulphonyl, where each of    the 4 last-mentioned radicals is unsubstituted or substituted by one    or more radicals from the group consisting of halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkyl.

More preferably

-   R¹ also represents a polycyclic radical based on (C₃-C₉)-cycloalkyl,    (C₅-C₉)-cycloalkenyl, (C₅-C₉)-cycloalkynyl or phenyl, where the base    ring is fused, preferably benzo-fused, with a carbocyclic or    heterocyclic ring, preferably a 5- or 6-membered ring having 0 or 1    to 3 ring heteroatoms from the group consisting of N, O and S, and    where the base ring or the polycyclic system is unsubstituted or    substituted by one or more radicals from the group consisting of    halogen, cyano, nitro, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₄)-alkylthio, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy,    [(C₁-C₄)-alkoxy]carbonyl and [(C₁-C₄)-haloalkoxy]carbonyl.

Preference is also given to compounds (I), preferably of the formula(Ia), or salts thereof in which

-   R¹ represents a saturated, partially unsaturated or heteroaromatic    heterocyclyl radical which has 3 to 9 ring atoms, preferably 5 or 6    ring atoms, which has 1 to 4 heteroatoms, preferably 1 to 3 ring    heteroatoms from the group consisting of N, O and S and which is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, cyano, thio, nitro, hydroxy, (C₁-C₆)-alkyl,    (C₁-C₆)-haloalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,    (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy,    (C₁-C₆)-haloalkoxy, (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy,    (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkoxy, [(C₁-C₈)-alkoxy]carbonyl,    [(C₁-C₆)-haloalkoxy]carbonyl and oxo.

Preference is also given to compounds (I), preferably of the formula(Ia), or salts thereof in which

-   R¹ represents a radical of the formula SiR^(a)R^(b)R^(c),    —NR^(a)R^(b) or —N═CR^(c)R^(d), preferably of the formula    —NR^(a)R^(b) or —N═CR^(c)R^(d), where in the 5 last-mentioned    formulae each of the radicals R^(a), R^(b), R^(c) and R^(d)    independently of the others represents hydrogen, (C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, benzyl, substituted benzyl, phenyl    or substituted phenyl, but where SiH₃ for SiR^(a)R^(b)R^(c) is    excluded, or R^(a) and R^(b) together with the nitrogen atom    represent a 3- to 8-membered heterocycle which, in addition to the    nitrogen atom, may contain one or two further ring heteroatoms from    the group consisting of N, O and S and which is unsubstituted or    substituted by one or more radicals from the group consisting of    (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, or R^(c) and R^(d) together    with the carbon atom represent a 3- to 8-membered carbocyclic    radical or heterocyclic radical which may contain 1 to 3 ring    heteroatoms from the group consisting of N, O and S, where the    carbocyclic or heterocyclic radical is unsubstituted or substituted    by one or more radicals from the group consisting of (C₁-C₄)-alkyl    and (C₁-C₄)-haloalkyl.

Particular preference is also given to compounds (I), preferably of theformula (Ia), or salts thereof in which

-   R¹ represents H, methyl, ethyl, n-propyl, isopropyl, n-butyl,    s-butyl, isobutyl, t-butyl, allyl, ethynyl,    propargyl(prop-2-yn-1-yl), prop-1-yn-1-yl, but-2-yn-1-yl,    but-3-yn-1-yl, 2-chloroprop-2-en-1-yl, 3-phenylprop-2-yn-1-yl,    3,3-dichloroprop-2-en-1-yl, 3,3-dichloro-2-fluoroprop-2-en-1-yl,    methylprop-2-yn-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,    but-3-en-1-yl, but-2-yn-1-yl, but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl,    3-methylbut-2-en-1-yl, 3-methylbut-1-en-1-yl,    1-(2E)-1-methylbut-2-en-1-yl, (E)-pent-3-en-2-yl or    (Z)-pent-3-en-2-yl,    -   phenyl, 2-carboxyphenyl, 2-chlorophenyl, 3-chlorophenyl,        4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,        3-methoxyphenyl, 4-methoxyphenyl, 2-methoxyphenyl,        3-methoxyphenyl, 4-methoxyphenyl, benzyl, 2-fluorobenzyl,        2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl,        2,3-difluorobenzyl, 2,4-difluorobenzyl, 2,5-difluorobenzyl,        2,6-difluorobenzyl, 3,4-difluorobenzyl, 3,5-difluorobenzyl,        2-phenylethyl, 1-phenylethyl, (4-chlorophenyl)methyl [i.e.        ═CH₂(4-Cl-Ph)=4-chlorobenzyl], (4-fluorophenyl)methyl [i.e.        ═CH₂(4-F-Ph)], (4-methoxyphenyl)methyl [i.e. ═CH₂(4-OMe-Ph)],        2-phenoxyethyl, 2-phenylthioethyl [=2-(phenylsulphanyl)ethyl],        2-phenylsulphinylethyl, 2-phenylsulphonylethyl,    -   trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl,        dichloromethyl, chloromethyl,    -   methoxymethyl, 2-methoxyethyl, 2,2,2-trifluoroethyl,        1,1,1-trifluoroprop-2-yl, 2,2-difluoroethyl,        1,3-difluoroprop-2-yl, 2,3-dimethoxypropyl,        2,3-dimethoxyprop-2-yl, 2,2-dimethoxyeth-2-yl,        2-(2,2,2-trifluoroethoxy)ethyl, 2-fluoroethyl, 2-chloroethyl,        2-bromoethyl, 2-iodoethyl, 2,2,3,3,3-pentafluoropropyl,        1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 2-hydroxyprop-1-yl,        3-hydroxypropyl, 3-hydroxyprop-2-yl,    -   (2-methoxyethoxy)methyl; 2-(2-methoxyethoxy)ethyl;        (2-ethoxyethoxy)methyl; 2-(2-ethoxyethoxy)ethyl,    -   (acetoxy)methyl, (propanoyloxy)methyl,        (2-methylpropanoyloxy)methyl, (2,2-dimethylpropanoyloxy)methyl,        1-(acetoxy)ethyl, 2-(acetoxy)ethyl, 2-(propanoyloxy)ethyl,        1-(propanoyloxy)ethyl, 1-(2-methylpropanoyloxy)eth-1-yl,        2-(2-methylpropanoyloxy)eth-1-yl,        2-(2,2-dimethylpropanoyloxy)ethyl [i.e.        1-(t-butylcarbonyloxy)ethyl], 2-(2,2-dimethylpropanoyloxy)ethyl;    -   1-(2,2-dimethylpropanoyloxy)-2-methylprop-1-yl,        1-(t-butylcarbonyloxy)-2-methylprop-1-yl,    -   (methoxycarbonyl)methyl, (ethoxycarbonyl)methyl,        (n-propoxycarbonyl)methyl, (i-propoxycarbonyl)methyl,        (n-butoxycarbonyl)methyl, (s-butoxycarbonyl)methyl,        (i-butoxycarbonyl)methyl, (t-butoxycarbonyl)methyl,        1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl,        1-(ethoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl,        1-(n-propoxycarbonyl)ethyl, 2-(n-propoxycarbonyl)ethyl,        1-(i-propoxycarbonyl)ethyl, 2-(i-propoxycarbonyl)ethyl,        1-(n-butoxycarbonyl)ethyl, 2-(n-butoxycarbonyl)ethyl,        1-(s-butoxycarbonyl)ethyl, 2-(s-butoxycarbonyl)ethyl,        1-(i-butoxycarbonyl)ethyl, 2-(i-butoxycarbonyl)ethyl,        1-(t-butoxycarbonyl)ethyl, 2-(t-butoxycarbonyl)ethyl,    -   (methoxycarbonyloxy)methyl, (ethoxycarbonyloxy)methyl,        (n-propoxycarbonyloxy)methyl, (i-propoxycarbonyloxy)methyl,        (n-butoxycarbonyloxy)methyl, (s-butoxycarbonyloxy)methyl,        (i-butoxycarbonyloxy)methyl, (t-butoxycarbonyloxy)methyl,        1-(methoxycarbonyloxy)ethyl, 2-(methoxycarbonyloxy)ethyl,        1-(ethoxycarbonyloxy)ethyl, 2-(ethoxycarbonyloxy)ethyl,        1-(n-propoxycarbonyloxy)ethyl, 2-(n-propoxycarbonyloxy)ethyl,        1-(i-propoxycarbonyloxy)ethyl, 2-(i-propoxycarbonyloxy)ethyl,        1-(n-butoxycarbonyloxy)ethyl, 2-(n-butoxycarbonyloxy)ethyl,        1-(s-butoxycarbonyloxy)ethyl, 2-(s-butoxycarbonyloxy)ethyl,        1-(i-butoxycarbonyloxy)ethyl, 2-(i-butoxycarbonyloxy)ethyl,        1-(t-butoxycarbonyloxy)ethyl, 2-(t-butoxycarbonyloxy)ethyl,        (cyclohexoxycarbonyloxy)methyl,        1-(cyclohexoxycarbonyloxy)eth-1-yl,        2-(cyclohexoxycarbonyloxy)eth-1-yl,    -   (acetyl)methyl, 1-(acetyl)ethyl, 2-(acetyl)ethyl,        1-(acetyl)propyl, 2-(acetyl)propyl, 3-(acetyl)propyl,        (propanoyl)methyl, 1-(propanoyl)ethyl, 2-(propanoyl)ethyl,        1-(propanoyl)propyl, 2-(propanoyl)propyl, 3-(propanoyl)propyl,        1-(propanoyl)-2-methylpropyl,    -   2-ethylthioethyl [=2-(ethylsulphanyl)ethyl],        2-(ethylsulphinyl)ethyl, 2-(ethylsulphonyl)ethyl,    -   2-(ethylideneaminooxy)ethyl, 2-(prop-2-ylideneaminooxy)ethyl,        2-(but-2-ylideneaminooxy)ethyl, 2-(pent-3-ylideneaminooxy)ethyl,        (N,N-dimethylamino)methyl, 2-(N,N-dimethylamino)eth-1-yl,        1-(N,N-dimethylamino)eth-1-yl, 2-(N,N-diethylamino)eth-1-yl,        1-(N,N-diethylamino)eth-1-yl, (N,N-diethylamino)methyl,    -   (N,N-dimethylaminocarbonyl)methyl,        1-(N,N-dimethylaminocarbonyl)ethyl,        2-(N,N-dimethylaminocarbonyl)ethyl,        (N,N-diethylaminocarbonyl)methyl,        1-(N,N-diethylaminocarbonyl)ethyl,        2-(N,N-diethylaminocarbonyl)ethyl, 1-(dimethylamino)prop-2-yl        [i.e. 2-(dimethylamino)-1-methylethyl],        1-(diethylamino)prop-2-yl,    -   trimethylsilylmethyl, 1-(trimethylsilyl)ethyl,        2-(trimethylsilyl)ethyl, triethylsilylmethyl,        1-(triethylsilyl)ethyl, 2-(triethylsilyl)ethyl, cyclopropyl,        cyclopropylmethyl, 1-cyclopropylethyl, 2-cyclopropylethyl,        (1-methylcyclopropyl)methyl, 1-(1-methylcyclopropyl)ethyl,        2-(1-methylcyclopropyl)ethyl, (2,2-dichlorocyclopropyl)methyl,        1-(2,2-dichlorocyclopropyl)ethyl,        2-(2,2-dichlorocyclopropyl)ethyl,        (2,2-dimethylcyclopropyl)methyl,        1-(2,2-dimethylcyclopropyl)ethyl,        2-(2,2-dimethylcyclopropyl)ethyl, cyclobutylmethyl,        cyclopentylmethyl, cyclohexylmethyl or    -   pyrid-2-yl, pyrid-3-yl, pyrid-4-yl, 2-chloropyrid-3-yl,        3-chloropyrid-2-yl, thien-2-yl, thien-3-yl, 2-chlorothien-3-yl,        3-chlorothien-2-yl, 4-chlorothien-2-yl, thietan-3-yl,    -   (1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl,        1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethyl,        2-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethyl,        (1-ethyl-3-methyl-1H-pyrazol-4-yl)methyl,        1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethyl,        2-(1-ethyl-3-methyl-1H-pyrazol-4-yl)ethyl, tetrahydrofuran-2-yl,        tetrahydrofuran-3-yl, tetrahydrofuran-2-ylmethyl,        tetrahydrofuran-3-ylmethyl,        (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl; oxetan-3-yl,        (oxetan-3-yl)methyl, (oxetan-2-yl)methyl,        (1,3-dioxolan-2-yl)methyl, (1,3-dioxolan-4-yl)methyl,        5-methyl-2-oxo-1,3-dioxolan-4-yl)methyl, (morpholin-4-yl)methyl;        1-(morpholin-4-yl)ethyl, 2-(morpholin-4-yl)ethyl,        2,3-dihydro-1H-inden-2-yl, dihydro-1H-inden-3-yl,        dihydro-1H-inden-4-yl, dihydro-1H-inden-5-yl, 1H-inden-2-yl,        1H-inden-3-yl, 1H-inden-4-yl, 1H-inden-5-yl, 1H-inden-6-yl or        1H-inden-7-yl.

Here, very particular preference is given to compounds (I), preferablyof the formula (Ia), and salts thereof in which

-   R¹ represents H, methyl, ethyl, n-propyl, isopropyl, n-butyl,    s-butyl, isobutyl, t-butyl, phenyl, benzyl, CH₂(4-Cl-Ph), i.e.    (4-chlorophenyl)methyl, CH₂(4-F-Ph), i.e. (4-fluorophenyl)methyl,    CH₂(4-OMe-Ph), i.e. (4-methoxyphenyl)methyl, 2-fluorobenzyl,    2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,3-difluorobenzyl,    2,4-difluorobenzyl, 2,5-difluorobenzyl, 2,6-difluorobenzyl,    3,4-difluorobenzyl, 3,5-difluorobenzyl, 2-phenoxyethyl,    2-ethylthioethyl, 2-ethylsulphinylethyl, 2-ethylsulphonylethyl,    2-phenylthioethyl, 2-phenylsulphinylethyl, 2-phenylsulphonylethyl,    methoxymethyl, 2-methoxyethyl, tetrahydrofuran-2-ylmethyl,    2-(dimethylamino)ethyl, oxetan-3-yl, (3-methyloxetan-3-yl)methyl,    thietan-3-yl, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl,    2,2-difluoroethyl, 2-fluoroethyl, 2,2,3,3,3-pentafluoropropyl,    cyclopropylmethyl, 1-cyclopropylethyl, (1-methylcyclopropyl)methyl,    (2,2-dichlorocyclopropyl)methyl, (2,2-dimethylcyclopropyl)methyl,    tetrahydrofuran-2-ylmethyl, allyl, ethynyl, propargyl    (=prop-2-yn-1-yl), prop-1-yn-1-yl, 2-chloroprop-2-en-1-yl,    3-phenylprop-2-yn-1-yl, 3,3-dichloroprop-2-en-1-yl,    3,3-dichloro-2-fluoroprop-2-en-1-yl, methylprop-2-yn-1-yl,    2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, but-2-yn-1-yl,    but-3-yn-1-yl, 4-chlorobut-2-yn-1-yl, 3-methylbut-2-en-1-yl,    3-methylbut-1-en-1-yl, 1-(2E)-1-methylbut-2-en-1-yl,    (E)-pent-3-en-2-yl or (Z)-pent-3-en-2-yl, cyclobutylmethyl,    cyclopentylmethyl, cyclohexylmethyl or    1-ethyl-5-methyl-1H-pyrazole-4-methyl, i.e.    (1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl.

Here, very particular preference is given to compounds (I), preferablyof the formula (Ia), and salts thereof in which

R¹ represents H, methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl,isobutyl, t-butyl, allyl and propargyl, in particular methyl or ethyl.

Preference is also given to compounds (I) in which

-   (R²)_(n) represents n substituents R²,    -   where R², if n=1, or each of the substituents R², if n is        greater than 1, independently of the others represents halogen,        cyano, nitro, hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio,        (C₁-C₆)-alkylsulphinyl, (C₁-C₆)-alkylsulphonyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkylthio,        (C₁-C₄)-haloalkylsulphinyl, (C₁-C₄)-haloalkylsulphonyl,        (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl which is optionally substituted by one or        more radicals from the group consisting of halogen and        (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkoxy which is optionally        substituted by one or more radicals from the group consisting of        halogen and (C₁-C₄)-alkyl, or a radical of the formula C(O)OR³,        C(O)NR⁴R⁵, C(O)—Het², NR⁶R⁷ or Het³    -   or where in each case two groups R² located ortho at the ring        together are a group of the formula -Z¹-A**-Z² in which    -   A** represents an alkylene group having 1 to 4 carbon atoms        which is optionally substituted by one or more radicals from the        group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z¹ represents a direct bond, O or S and    -   Z² represents a direct bond, O or S, where the group -Z¹-A**-Z²        together with the carbon atoms, attached to the group, of the        phenyl ring form a fused-on 5- or 6-membered ring,-   R³ represents hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl or the group M mentioned,-   R⁴, R⁵, R⁶, R⁷, Het² and Het³ have the meanings mentioned,    preferably-   R⁴, R⁵, R⁶ and R⁷ independently of one another each represent    hydrogen or (C₁-C₄)-alkyl which is unsubstituted or substituted by    one or more radicals from the group consisting of halogen, nitro,    cyano and phenyl, or    -   (C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentioned        radicals in each case independently of the other is        unsubstituted or substituted by one or more radicals from the        group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        phenyl and benzyl,-   Het² and Het³ independently of one another each represent a    saturated or partially unsaturated radical of a heterocycle having 3    to 6 ring atoms and at least one nitrogen atom as ring heteroatom at    position 1 of the ring and optionally 1, 2 or 3 further ring    heteroatoms from the group consisting of N, O and S, where the    radical of the heterocycle is attached at the nitrogen atom in    position 1 of the ring to the remainder of the molecule of the    compound of the formula (I) and where the heterocycle is    unsubstituted or substituted by one or more radicals from the group    consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and oxo,    preferably the radical of a saturated heterocycle of the type    mentioned, in particular a morpholino, piperidino or pyrrolidino    group, and-   n represents 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4, in particular    1, 2 or 3.

Here, more preference is given to compounds (I) in which

-   (R²)_(n) represents n substituents R²,    -   where R², if n=1, or each of the substituents R², if n is        greater than 1, independently of the others represents halogen,        cyano, nitro, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-haloalkylthio, (C_(r) C₄)-haloalkylsulphinyl,        (C₁-C₄)-haloalkylsulphonyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₃-C₆)-cycloalkyl, or a radical of the formula C(O)OR³,        C(O)NR⁴R⁵, C(O)—Het², NR⁶R⁷ or Het³,    -   or where in each case two groups R² located ortho at the ring        together are a group of the formula -Z¹-A**-Z² in which    -   A** represents an alkylene group having 1 to 4 carbon atoms        which is optionally substituted by one or more radicals from the        group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy,    -   Z¹ represents a direct bond, O or S and    -   Z² represents a direct bond, O or S, where the group -Z¹-A**-Z²        together with the carbon atoms, attached to the group, of the        phenyl ring form a fused-on 5- or 6-membered ring,-   R³ represents hydrogen, (C₁-C₄)-alkyl or the group M mentioned,-   R⁴, R⁵, R⁶, R⁷, Het² and Het³ have the meanings mentioned,    preferably R⁴, R⁵, R⁶ and R⁷ independently of one another each    represent hydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, benzyl,    (C₃-C₆)-cycloalkyl or phenyl,-   Het² and Het³ independently of one another each represent a    morpholino, piperidino or pyrrolidino group and-   n represents 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4, in particular    1, 2 or 3.

Here, more preference is given to compounds (I) in which

-   (R²)_(n) represents n substituents R²,-   where R², if n=1, or each of the substituents R², if n is greater    than 1, independently of the others represents halogen, cyano,    nitro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio,    (C₁-C₂)-alkylsulphinyl, (C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl,    (C₁-C₂)-haloalkoxy, (C₁-C₂)-haloalkylthio,    (C₁-C₂)-haloalkylsulphinyl, (C₁-C₂)-haloalkylsulphonyl or    (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl, in particular each of the substituents    R² independently of the others represents halogen, such as fluorine,    chlorine, bromine or iodine, or cyano, nitro, methyl, methoxy,    methylthio, methylsulphinyl, methylsulphonyl, trifluoromethyl,    trifluoromethoxy, difluoromethoxy, trifluoroalkylthio,    trifluoromethylsulphinyl or trifluoromethylsulphonyl, in particular    cyano, nitro or halogen such as fluorine, chlorine or bromine, and-   n represents 1, 2, 3, 4 or 5, preferably 1, 2, 3 or 4, in particular    1, 2 or 3.

More preference is given to compounds of the formula (I) or saltsthereof in which

-   (R²)_(n) represents 2-bromo, 3-bromo, 4-bromo, 2-chloro, 3-chloro,    4-chloro, 2-fluoro, 3-fluoro, 4-fluoro, 2-cyano, 3-cyano, 4-cyano,    2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF₃,    3-CF₃, 4-CF₃, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy,    4-ethoxy, 2-trifluoromethoxy, 3-trifluoromethoxy,    4-trifluoromethoxy, 2-difluoromethoxy, 3-difluoromethoxy,    4-difluoromethoxy, 2-methylthio, 3-methylthio, 4-methylthio,    2-methylsulphinyl, 3-methylsulphinyl, 4-methylsulphonyl,    2-methylsulphonyl, 3-methylsulphonyl, 4-methylsulphonyl, 2-nitro,    3-nitro, 4-nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl,    2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluoro,    2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro,    3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro,    2,6-dichloro, 3,4-dichloro, 3,5-dichloro, 2,5-dicyano, 2,6-dicyano,    (2-Cl-3-F), (2-Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F),    (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F),    (4-Br-2-F), (4-Br-3-F), (4-CN-3-F), (4-NO₂-3-F), (3-CN-4-F),    (3-NO₂-4-F), (3-CN-4-Cl), (3-NO₂-4-Cl), (5-CN-2-F), 2,3,4-trifluoro,    2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro,    2,3,4-trichloro, 2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro,    3,4,5-trichloro or else (2,6-difluoro-4-Cl), 2,5-dicyano,    2,6-dicyano, (4-methoxy-3-F), where the numbering of the radicals    refers to the position of the radical at the phenyl-1-yl radical in    which the carbon atom attached in the 3-position at the butyric acid    skeleton has the 1-position in the ring.

More preference is given to compounds of the formula (I) or saltsthereof in which

-   (R²)_(n) represents 2-cyano, 3-cyano, 4-cyano, 2-bromo, 3-bromo,    4-bromo, 2-chloro, 3-chloro, 4-chloro, 2-fluoro, 3-fluoro, 4-fluoro,    2-nitro, 3-nitro, 4-nitro, 2-methoxy, 3-methoxy, 4-methoxy,    2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro,    3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4-dichloro, 2,5-dichloro    2,6-dichloro, 3,4-dichloro, 3,5-dichloro, (2-Cl-3-F), (2-Cl-4-F),    (2-Cl-5-F), (2-Cl-6-F), (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F),    (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F), (4-Br-2-F), (4-Br-3-F),    (4-CN-3-F), (4-NO₂-3-F), 2,3,4-trifluoro, 2,3,5-trifluoro,    2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4-trichloro,    2,3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro    or else (2,6-difluoro-4-Cl), 2,5-dicyano, 2,6-dicyano,    (4-methoxy-3-F), where the numbering of the radicals refers to the    position of the radical at the phenyl-1-yl radical in which the    carbon atom attached in the 3-position at the butyric acid skeleton    has the 1-position in the ring.

More preference is also given here to compounds of the formula (I) orsalts thereof in which

-   (R²)_(n) represents 3-chloro, 4-chloro, 2-fluoro, 3-fluoro,    4-fluoro, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro,    3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-2-F),    (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F) or also    (2,6-difluoro-4-Cl).

Here, particular preference is given to:

Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3-chloro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 4-chloro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2-fluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3-fluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 4-fluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,3-difluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,4-difluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,5-difluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 2,6-difluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3,4-difluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents 3,5-difluoro.Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-2-F).Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-4-F).Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-5-F).Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (3-Cl-6-F).Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (4-Cl-2-F).Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (4-Cl-3-F).Compounds of the formula (I) or salts thereof in which (R²)_(n)represents (2,6-difluoro-4-Cl).

The invention also includes all tautomers, such as keto and enoltautomers, and their mixtures and salts, if appropriate functionalgroups are present.

The present invention also provides processes for preparing thecompounds of the general formula (I) or (Ia) and/or their salts. Thisincludes processes which can be carried out analogously to knownmethods.

To prepare the compounds (I) according to the invention, it is possibleto use initially the corresponding diastereomer mixtures in the form oftheir racemic mixtures. The preparation of the diastereomer mixtures ofthe cyanobutyrates is known in principle; see, for example, EP-A 5341,EP-A 266725, EP-A270 830, JP 04/297454, JP 04/297455, JP 05/058979, WO2011/003776, WO 2011/003775, WO 2011/042378, WO 2011/073143, WO2011/098417.

Analogously to the synthesis routes described in the publications cited,the compounds can be prepared by standard processes of organicchemistry.

Diastereomer mixtures of the compounds of the formula (I) comprising thecompound (I) to be prepared are obtained, for example, in that

(a) compounds of the formula (II)(“3-cyanomethylpyridine”/“3-pyridylacetonitrile”)

-   -   are reacted with compounds of the formula (III) (cinnamic acid        derivatives) or salts thereof

-   -   to give compounds of the formula (I) (diastereomers/racemic)

-   -   where R¹, R² and n in the compounds (II) and (III) are as        defined in the respective compound of the formula (I) to be        prepared.

In the process mentioned above and in the processes below, in some casessolvents are employed. In this context, “inert solvents” refers in eachcase to solvents which are inert under the particular reactionconditions, but which do not have to be inert under any reactionconditions.

The processes described in each case can be carried out in apparatusescustomary in the laboratory, in pilot plants and in plants for preparingcommercial amounts and industrial processes, or alternatively also in amicrowave oven.

The starting materials (II) and (III) required for preparing thecompounds (I) are commercially available, known from the literaturecited above or can be prepared analogously to the processes described inthe cited literature.

The reaction according to variant (a) can be carried out, for example,according to methods and under conditions like those known for Michaeladditions. The reaction is carried out, for example, at temperatures offrom −100° C. to 150° C., preferably from −78° C. to 100° C., in anorganic or inorganic solvent, generally in the presence of a base or acatalyst or both [cf. J. Chem. Soc. (1945), p. 438].

Suitable solvents are, for example, organic solvents such as:

-   -   aliphatic hydrocarbons such as pentane, hexane, cyclohexane or        petroleum ether;    -   aromatic hydrocarbons such as toluene, o-, m- or p-xylene,    -   halogenated hydrocarbons such as methylene chloride, chloroform        or chlorobenzene,    -   ethers, such as diethyl ether, diisopropyl ether, tert-butyl        methyl ether, dioxane, anisole and tetrahydrofuran (THF),    -   nitriles such as acetonitrile or propionitrile,    -   ketones such as acetone, methyl ethyl ketone, diethyl ketone and        tert-butyl methyl ketone,    -   alcohols such as methanol, ethanol, n-propanol, isopropanol,        n-butanol and tert-butanol, and also    -   dimethyl sulphoxide, dimethylformamide, dimethylacetamide,        sulpholane,    -   mixtures of the organic solvents mentioned.

In individual cases, it is also appropriate to use inorganic solventssuch as water or mixtures of organic solvents with water.

Preferred solvents are THF, toluene and methanol, and mixtures thereofwith other organic solvents.

The reaction according to preparation variant (a) is preferably carriedout in the presence of a base, for example from the group of theinorganic compounds such as the alkali metal and alkaline earth metalhydroxides, for example lithium hydroxide, sodium hydroxide, potassiumhydroxide or calcium hydroxide, the alkali metal and alkaline earthmetal oxides, for example lithium oxide, sodium oxide, calcium oxide ormagnesium oxide, the alkali metal and alkaline earth metal hydrides, forexample lithium hydride, sodium hydride, potassium hydride or calciumhydride, the alkali metal amides, for example lithium amide, sodiumamide or potassium amide, the alkali metal and alkaline earth metalcarbonates, for example lithium carbonate, potassium carbonate orcalcium carbonate, the alkali metal bicarbonates, for example sodiumbicarbonate, or the organometallic compounds such as, preferably, thealkali metal alkyls, for example methyllithium, butyllithium orphenyllithium, the alkylmagnesium halides, for example methylmagnesiumchloride, or the alkali metal and alkaline earth metal alkoxides, forexample sodium methoxide, sodium ethoxide, potassium ethoxide, potassiumtert-butoxide or dimethoxymagnesium.

The bases used can also be organic bases, for example from the group ofthe tertiary aliphatic amines, for example trimethylamine,triethylamine, tributylamine, diisopropylethylamine orN-methylpiperidine, or the aromatic tertiary amines, for examplepyridine or substituted pyridines such as collidine, lutidine or4-dimethylaminopyridine, or the bicyclic amines such as7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene or1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Preferred bases are, forexample, potassium tert-butoxide, lithium bis(trimethylsilyl)amide, DBUor 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene. The amount of base maygenerally be varied within wide limits. For example, it may be expedientto employ the base in catalytic amounts, in substoichiometric amounts,in equimolar amounts or in excess. A preferably liquid organic base mayoptionally also be used as solvent.

Suitable catalysts for the Michael addition according to variant (a) areacidic catalysts, for example from the group of the inorganic acids, forexample Broensted acids, such as hydrofluoric acid, hydrochloric acid,hydrobromic acid, sulphuric acid or perchloric acid, or Lewis acids,such as boron trifluoride, aluminium trichloride, iron(III) chloride,tin(IV) chloride, titanium(IV) chloride, scandium(III) triflate orzinc(II) chloride, and also the organic acids, for example formic acid,acetic acid, propionic acid, oxalic acid, toluenesulphonic acid,benzenesulphonic acid, camphorsulphonic acid, citric acid ortrifluoroacetic acid.

The amount of acidic catalyst may generally be varied within widelimits. For example, it may be expedient to employ the acid in catalyticamounts, in substoichiometric amounts, in equimolar amounts or inexcess. A preferably liquid acid may optionally also be used as solvent.

Variant (a1) for the preparation of the intermediate of the formula(II): Compounds of the formula (II) and salts thereof are also obtained,for example, by process [variant (a1)], characterized in that apyridinecarboxylic acid of the formula (IV) or its ester of the formula(V),

where the radical R in the formula (V) represents a hydrocarbon radical,preferably (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl or(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, in particular methyl or ethyl, is reducedto give the compound of the formula (VI) (=reduction at the acid orester group),

and the compound (VI) is converted into the compound (VII),

where X represents a leaving group, for example halogen, such aschlorine, bromine or iodine, obtained by a halogenation reaction suchas, for example, substitution by halide, or sulphonates of the formula—O—SO₂—R(R═(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, phenyl, which is optionallysubstituted, for example by halogen, nitro or alkyl), for examplemesylate (R=methyl), triflate (R═CF₃), tosylate (R=p-tolyl), bromylate(R=p-bromophenyl), nosylat (R=p-nitrophenyl), obtained by esterificationof an appropriate sulphonyl chloride with compounds of the formula (VI),and the compound (VII) is converted by substitution with cyanide intothe compound (II).

The individual synthesis steps according to variant (al) are known inprinciple to the person skilled in the art and described, for example,in Acta Pharm. Suecica 1972, 9, 411-418; J. Org. Chem. 1999, 64 (23),8576-8581; Synthesis 1998, 9, 1335-1338; J. Med. Chem. 2000, 43 (18)3386-3399; U.S. Pat. No. 5,225,423 (Shell Research Limited 1993), U.S.Pat. No. 4,966,902 (Hoechst AG, 1990); WO2007/045989 (Pfizer Limited,2007); US2004/242572 (Boehringer Ingelheim International GmbH, 2004) andthe literature cited therein.

Diastereomer mixtures or racemic diastereomers of the compounds of theformula (I) can be obtained according to variant (b) bytransesterification, characterized in that (b) compounds of the formula(I*)

in which R is a radical from the group of the radicals possible for R¹,but different from the radical R¹ in the compound (I) to be prepared,are reacted with a compound of the formula R¹—OH, in which R¹ is definedas in formula (I), to give the compound (I), where R² and n in thecompound (I*) are as defined in the respective compound of the formula(I) to be prepared.

In a particular embodiment, according to variant (b1) it is alsopossible to obtain, as compounds (I), stereochemically enrichedcompounds of the abovementioned formula (Ia), characterized in that

-   (b1) stereochemically enriched compounds of the formula (Ia*), which    correspond stereochemically [i.e. are at least as enriched as in the    desired compound (Ia)]

-   -   in which R is a radical from the group of the radicals possible        for R¹, but different from the radical R¹ in the compound (la)        to be prepared, are reacted with a compound of the formula R¹—OH        in which R¹ is defined as in the compound of the formula (Ia) to        be prepared.

The transesterifications (b) and (b1) can be carried out, for example,using a suitable alcohol R¹—OH in the presence of a catalyst, optionallyin the presence of an aprotic solvent. Furthermore, in general, thoseconditions are advantageous where the chemical equilibrium is shifted tothe side of the desired product, for example using a large excess of thealcohol R¹—OH under virtually anhydrous conditions, for example in thepresence of a molecular sieve.

The reactions (transesterifications) can generally be carried out attemperatures of from 0° C. to 180° C., preferably from 20° C. to 100°C., in the presence of a Lewis or Broensted acid or an enzyme [cf. J.Org. Chem. 2002, 67, 431].

Suitable solvents are, for example, organic aprotic solvents such as:

-   -   aliphatic hydrocarbons such as pentane, hexane, cyclohexane or        petroleum ether;    -   aromatic hydrocarbons such as toluene, o-, m- or p-xylene,    -   halogenated hydrocarbons such as methylene chloride        (dichloromethane), chloroform or chlorobenzene,    -   ethers, such as diethyl ether, diisopropyl ether, tert-butyl        methyl ether, dioxane, anisole or tetrahydrofuran (THF),    -   nitriles such as acetonitrile or propionitrile,    -   ketones such as acetone, methyl ethyl ketone, diethyl ketone and        tert-butyl methyl ketone,    -   dimethyl sulphoxide, dimethylformamide, dimethylacetamide or        sulpholane or    -   mixtures of the organic solvents mentioned.

The preferred solvent is the alcohol R¹—OH, which is at the same timeused as reaction partner for the transesterification, optionally incombination with one of the aprotic organic solvents mentioned.

Alternatively, it is also possible to obtain the desired ester fromanother ester in two steps by acidic or basic hydrolysis of the otherester to the free acid, i.e. to compounds (I*) or (Ia*), in which R isin each case H, and subsequent esterification with an alcohol R¹—OH.

Variants (c) and (c1):

The preparation of diastereomer mixtures or racemic diastereomers of theformula (I) according to variant (c) or optically active compounds (Ia)according to variant (c1) is therefore characterized in that a compoundof the abovementioned formula (I*) or the formula (Ia*) in which theradicals R are each hydrogen (free carboxylic acids) is esterified withan alcohol of the formula R¹—OH by customary methods, if appropriatecombined with a previous preparation (c-1) or (c1-1) of the free acidfrom another ester of the formula (I*) or the formula (Ia*) in which theradicals R are each not hydrogen.

The esterification from the free acid of the formula (I*)/R═H or(Ia*)/R═H can be carried out, for example, analogously to customarymethods, for example at temperatures of from 0° C. to 120° C.,preferably from 20° C. to 50° C., optionally in the presence of acatalyst, in a substantially anhydrous medium or under conditions wherethe water including the water formed during the esterification is boundor otherwise removed. Suitable catalysts are anhydrous acids and bases,preferably organic acids or bases; see handbooks for chemical processesfor esterifying carboxylic acids; see also, for example, J. Am. Chem.Soc. 2007,129 (43), 13321; J. Org. Chem. 1984,49 (22), 4287.

Suitable solvents for the esterification are the aprotic organicsolvents mentioned above for process variants (b) and (b1), includingthe alcohol R¹—OH which is at the same time used as a reaction partnerfor the esterification, optionally in combination with one of theaprotic organic solvents mentioned.

Suitable catalysts for the esterification are the bases or acidic orbasic catalysts mentioned for process variant (a) mentioned (Michaeladdition), in anhydrous form or with a water content which is as low aspossible. Preferred catalysts are the bases lithium hydroxide, potassiumcarbonate or organic amines such as pyridines, substituted pyridines andDBU.

Any hydrolysis carried out before the esterification [process variants(c-1) and (c1-1)] of other esters of the formula (I*) or the formula(Ia*), where R is in each case not H, can be carried out analogously tocustomary methods, for example at temperatures of from 0° C. to 120° C.,preferably from 20° C. to 50° C., if appropriate in the presence of acatalyst, in a water-containing medium/solvent; see handbooks onchemical processes for hydrolysing carboxylic esters; see also, forexample, J. Am. Chem. Soc. 2007,129 (43), 13321; J. Org. Chem. 1984,49(22), 4287.

A suitable solvent for the hydrolysis [process variants (c-1) and(c1-1)] is water or a water-containing organic solvent, for examplebased on the organic solvent mentioned for process variant (a) mentioned(Michael addition), preferably water or polar organic solventscontaining water, such as THF.

Suitable catalysts for the hydrolysis are the acids, bases or acidic orbasic catalysts mentioned for process variant (a) mentioned (Michaeladdition), in each case containing water. Preferred catalysts areaqueous acids and bases, in particular bases such as lithium hydroxide,sodium hydroxide, potassium carbonate, pyridines, substituted pyridinesand DBU in the presence of organic solvents.

The catalysts for the esterification or the hydrolysis can generally beemployed in catalytic amounts. In general, it is also possible to userelatively large amounts including equimolar amounts and a molar excess.Frequently, a use as solvent is also possible.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separating the phases and, if appropriate,chromatographic purification of the crude products. Some of theintermediates and end products are obtained in the form of colourless orslightly brownish viscous oils which are purified or freed from volatilecomponents under reduced pressure and at moderately elevatedtemperature.

If the intermediates and end products are obtained as solids, thepurification can also be carried out by recrystallization or digestion.If individual compounds (I) or (Ia) cannot be obtained by the routesdescribed above, they can be prepared by derivatization of othercompounds (I) or (Ia).

To prepare the erythro compounds, threo compounds or optically activeerythro or threo compounds according to the invention, preferably thethreo compounds (Ia), from the diastereomer mixtures of the compounds(I), it is necessary to enrich the respective diastereomer, for examplethe threo isomer or the stereoisomer (enantiomer) erythro-1, erythro-2,threo-1 or threo-2, preferably threo-2, from the mixture of thestereoisomers in an appropriate manner. Accordingly, an expedientprocess comprises the initial isolation of the erythro-1 and erythro-2or threo isomers threo-1 and threo-2 from the diastereomer mixture ofthe compounds of the formula (I) which still comprises the otherisomers, and optionally the subsequent optical resolution with isolationor enrichment of the desired enantiomer from the mixture with the otherenantiomers.

In an analogous manner, the erythro isomers can also be obtained as aracemic mixture and as enantiomers erythro-1 and erythro-2.

The isolation of the erythro or threo isomers as a racemic mixture canbe carried out analogously to the customary separation and purificationprocesses mentioned above (diastereomer separation).

Suitable for the subsequent preparation of compounds of the opticallyactive compounds (I), preferably of the formula (Ia), are methods foroptical resolution generally known to the person skilled in the art fromanalogous cases (cf. handbooks of stereochemistry), for examplefollowing processes for separating mixtures into diastereomers, forexample by physical processes, such as crystallization, chromatographicprocesses, in particular column chromatography and high-pressure liquidchromatography, distillation, if appropriate under reduced pressure,extraction and other processes; it is possible to separate remainingmixtures of enantiomers, generally by chromatographic separation onchiral solid phases. Suitable for preparative amounts or on anindustrial scale are processes such as the crystallization ofdiastereomeric salts which can be obtained from the diastereomermixtures using optically active acids and, if appropriate, provided thatacidic groups are present, using optically active bases.

Optically active acids which are suitable for optical resolution bycrystallization of diastereomeric salts are, for example,camphorsulphonic acid, camphoric acid, bromocamphorsulphonic acid,quinic acid, tartaric acid, dibenzoyltartaric acid and other analogousacids; suitable optically active bases are, for example, quinine,cinchonine, quinidine, brucine, 1-(S)- or 1-(R)-phenylethylamine andother analogous bases.

The crystallizations are then in most cases carried out in aqueous,alcoholic or aqueous-organic solvents, where the diastereomer which isless soluble precipitates first, if appropriate after seeding. Oneenantiomer of the compound of the formula (I) is then liberated from theprecipitated salt, or the other is liberated from the crystals, byacidification or using a base.

Accordingly, the invention also provides the process for preparing theoptically active compounds (I) [variant (d)], preferably (Ia),characterized in that (d) an optical resolution is carried out withcompounds (I), preferably the erythro compounds or in particular thethreo compounds of the formula (I), and the desired enantiomer,preferably the compound (Ia), is isolated in a stereochemical purity offrom 60 to 100%, preferably from 70 to 100%, more preferably from 80 to100%, in particular from 90 to 100%, based on the mixture of the erythroand threo enantiomers present.

As an alternative to the optical resolution methods mentioned,enantioselective processes starting with stereochemically pure startingmaterials are in principle also suitable for preparing the opticallyactive enantiomers, preferably the threo-2-enantiomers (Ia).

The following acids are generally suitable for preparing the acidaddition salts of the compounds of the formula (I): hydrohalic acids,such as hydrochloric acid or hydrobromic acid, furthermore phosphoricacid, nitric acid, sulphuric acid, mono- or bifunctional carboxylicacids and hydroxycarboxylic acids, such as acetic acid, maleic acid,succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid,sorbic acid, or lactic acid, and also sulphonic acids, such asp-toluenesulphonic acid and 1,5-naphthalenedisulphonic acid. The acidaddition compounds of the formula (I) can be obtained in a simple mannerby the customary methods for forming salts, for example by dissolving acompound of the formula (I) in a suitable organic solvent, such as, forexample, methanol, acetone, methylene chloride or benzene, and addingthe acid at temperatures of from 0 to 100° C., and they can be isolatedin a known manner, for example by filtration, and, if appropriate,purified by washing with an inert organic solvent.

The base addition salts of the compounds of the formula (I) arepreferably prepared in inert polar solvents, such as, for example,water, methanol or acetone, at temperatures of from 0 to 100° C.Examples of bases which are suitable for the preparation of the saltsaccording to the invention are alkali metal carbonates, such aspotassium carbonate, alkali metal hydroxides and alkaline earth metalhydroxides, for example NaOH or KOH, alkali metal hydrides and alkalineearth metal hydrides, for example NaH, alkali metal alkoxides andalkaline earth metal alkoxides, for example sodium methoxide orpotassium tert-butoxide, or ammonia, ethanolamine or quaternary ammoniumhydroxide of the formula [NRR′R″R″′]+OH⁻.

Collections of compounds of the formula (I) which can be synthesized bythe aforementioned processes can also be prepared in a parallel manner,it being possible for this to take place in a manual, partly automatedor completely automated manner. In this connection, it is possible toautomate the reaction procedure, the work-up or the purification of theproducts and/or intermediates. Overall, this is understood as meaning aprocedure as described, for example, by S. H. DeWitt in “Annual Reportsin Combinatorial Chemistry and Molecular Diversity: AutomatedSynthesis”, Volume 1, Verlag Escom, 1997, pages 69 to 77.

For the parallel reaction procedure and work-up, it is possible to use arange of commercially available instruments, of the kind offered by, forexample, the companies Stem Corporation, Woodrolfe Road, Tollesbury,Essex, CM9 8SE, England, or H+P Labortechnik GmbH, Bruckmannring 28,85764 Oberschlei Bheim, Germany. For the parallel purification ofcompounds (I) or of intermediates produced during the preparation, thereare available, inter alia, chromatography apparatuses, for example fromISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA. Theapparatuses listed allow a modular procedure in which the individualprocess steps are automated, but between the process steps manualoperations have to be carried out. This can be circumvented by usingpartly or completely integrated automation systems in which therespective automation modules are operated, for example, by robots.Automation systems of this type can be acquired, for example, fromZymark Corporation, Zymark Center, Hopkinton, Mass. 01748, USA.

Besides the methods described here, the preparation of compounds of theformula (I) can take place completely or partially bysolid-phase-supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bound to a synthesis resin.Solid-phase-supported synthesis methods are described extensively in thespecialist literature, for example Barry A. Bunin in “The CombinatorialIndex”, Academic Press, 1998. The use of solid-phase-supported synthesismethods permits a number of protocols, which are known from theliterature and which for their part may be performed manually or in anautomated manner, to be carried out. For example, the “teabag method”(Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad.Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 NorthTorrey Pines Road, La Jolla, Calif. 92037, USA, are employed, may besemiautomated. The automation of solid-phase-supported parallelsyntheses is performed successfully, for example, by apparatuses fromArgonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif.94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.

The preparation according to the processes described herein producescompounds of the formula (I) in the form of substance collections orlibraries. Accordingly, the present invention also provides libraries ofthe compounds of the formula (I) which comprise at least two compoundsof the formula (I), and precursors thereof.

The compounds of the formula (I) according to the invention (and/ortheir salts), above and hereinbelow also referred to together as“compounds according to the invention”, “compounds (I) according to theinvention” or in short as “compounds (I)”, have excellent herbicidalefficacy against a broad spectrum of economically importantmonocotyledonous and dicotyledonous annual harmful plants. The activecompounds also have good control over perennial harmful plants which aredifficult to control and produce shoots from rhizomes, root stocks orother perennial organs.

The present invention therefore also relates to a method for controllingunwanted plants or for regulating the growth of plants, preferably incrops of plants, where one or more compound(s) according to theinvention is/are applied to the plants (for example harmful plants suchas monocotyledonous or dicotyledonous weeds or undesired crop plants),to the seed (for example grains, seeds or vegetative propagules such astubers or shoot parts with buds), to the soil in or on which the plantsgrow (for example the soil of cropland or non-cropland) or to the areaon which the plants grow (for example the area under cultivation). Inthis context, the compounds according to the invention can be appliedfor example in pre-sowing (if appropriate also by incorporation into thesoil), pre-emergence or post-emergence methods. Specific examples may bementioned of some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compoundsaccording to the invention, without the enumeration being restricted tocertain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, lschaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

When the compounds according to the invention are applied to the soilsurface before germination, either the weed seedlings are preventedcompletely from emerging or the weeds grow until they have reached thecotyledon stage, but then stop growing and eventually, after three tofour weeks have elapsed, die completely.

If the active ingredients are applied post-emergence to the green partsof the plants, growth stops after the treatment, and the harmful plantsremain at the growth stage of the time of application, or die completelyafter a certain time, such that competition by the weeds, which isharmful to the crop plants, is thereby eliminated very early and in alasting manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia,or monocotyledonous crops of the genera Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, in particular Zea and Triticum, are damaged only to aninsignificant extent, or not at all, depending on the structure of therespective compound according to the invention and its application rate.For these reasons, the present compounds are very suitable for selectivecontrol of unwanted plant growth in plant crops such as agriculturallyuseful plants or ornamentals.

In addition, the compounds according to the invention (depending ontheir particular structure and the application rate deployed) haveoutstanding growth-regulating properties in crop plants. They interveneto regulate the plant's metabolism and can thus be used for controlledinfluence on plant constituents and to facilitate harvesting, forexample by triggering desiccation and stunted growth. In addition, theyare also suitable for general control and inhibition of unwantedvegetative growth without killing the plants. Inhibiting the vegetativegrowth plays an important role in many monocotyledonous anddicotyledonous crops since for example lodging can be reduced, orprevented completely, hereby.

By virtue of their herbicidal and plant-growth-regulating properties,the active compounds can also be used for control of harmful plants incrops of genetically modified plants or plants modified by conventionalmutagenesis. In general, transgenic plants are notable for specialadvantageous properties, for example for resistances to certainpesticides, in particular certain herbicides, resistances to plantdiseases or organisms that cause plant diseases, such as certain insectsor microorganisms such as fungi, bacteria or viruses. Other specificcharacteristics relate, for example, to the harvested material withregard to quantity, quality, storability, composition and specificconstituents. Thus, transgenic plants are known whose starch content isincreased, or whose starch quality is altered, or those where theharvested material has a different fatty acid composition.

It is preferred with a view to transgenic crops to use the compoundsaccording to the invention and/or their salts in economically importanttransgenic crops of useful plants and ornamentals, for example ofcereals such as wheat, barley, rye, oats, millet, rice and maize or elsecrops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peasand other vegetables.

It is also preferred to employ the compounds according to the inventionas herbicides in crops of useful plants which are resistant, or havebeen made resistant by recombinant means, to the phytotoxic effects ofthe herbicides.

By virtue of their herbicidal and plant-growth-regulatory properties,the active compounds can also be employed for controlling harmful plantsin crops of known genetically modified plants or genetically modifiedplants still to be developed. In general, transgenic plants are notablefor special advantageous properties, for example for resistances tocertain pesticides, in particular certain herbicides, resistances toplant diseases or organisms that cause plant diseases, such as certaininsects or microorganisms such as fungi, bacteria or viruses. Otherspecific characteristics relate, for example, to the harvested materialwith regard to quantity, quality, storability, composition and specificconstituents. Thus, transgenic plants are known whose starch content isincreased, or whose starch quality is altered, or those where theharvested material has a different fatty acid composition. Otherparticular properties may be tolerance or resistance to abioticstressors, for example heat, low temperatures, drought, salinity andultraviolet radiation.

It is preferred to use the compounds of the formula (I) according to theinvention or salts thereof in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet, rice, cassaya and maize or else crops ofsugar beet, cotton, soybean, oilseed rape, potato, tomato, peas andother vegetables.

It is preferred to employ the compounds of the formula (I) as herbicidesin crops of useful plants which are resistant, or have been maderesistant by recombinant means, to the phytotoxic effects of theherbicides.

Conventional ways of producing novel plants which have modifiedproperties in comparison to plants which have occurred to date consist,for example, in traditional breeding methods and the generation ofmutants. Alternatively, novel plants with altered properties can begenerated with the aid of recombinant methods (see, for example,EP-A-0221044, EP-A-0131624). For example, the following have beendescribed in several cases:

-   -   recombinant modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (for example WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to particular        herbicides of the glufosinate type (cf., for example,        EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or        the sulphonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, which is capable of        producing Bacillus thuringiensis toxins (Bt toxins), which make        the plants resistant to certain pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants with reduced photorespiration which        feature higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which feature higher yields or better        quality,    -   transgenic crop plants which feature a combination, for example,        of the abovementioned novel properties (“gene stacking”).

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg, or Christou, “Trends in Plant Science” 1(1996) 423-431.

To carry out such recombinant manipulations, nucleic acid moleculeswhich allow mutagenesis or a sequence change by recombination of DNAsequences can be introduced into plasmids. For example, basesubstitutions can be carried out, part-sequences can be removed, ornatural or synthetic sequences may be added with the aid of standardmethods. For the joining of the DNA fragments to one another, adaptorsor linkers can be attached to the fragments; see, for example, Sambrooket al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. ColdSpring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker“Gene and Klone” [Genes and Clones], VCH Weinheim 2nd edition 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the abovementioned gene product. To this end, itis possible to use DNA molecules which encompass the entire codingsequence of a gene product inclusive of any flanking sequences which maybe present, and also DNA molecules which only encompass portions of thecoding sequence, it being necessary for these portions to be long enoughto have an antisense effect in the cells. The use of DNA sequences whichhave a high degree of homology to the coding sequences of a geneproduct, but are not completely identical to them, is also possible.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any compartment of the plant cell.However, in order to achieve localization in a particular compartment,it is possible, for example, to join the coding region to DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants can beplants of any desired plant species, i.e. not only monocotyledonous, butalso dicotyledonous, plants.

For instance, it is possible to obtain transgenic plants whoseproperties are altered by overexpression, suppression or inhibition ofhomologous (=natural) genes or gene sequences, or expression ofheterologous (=foreign) genes or gene sequences. It is preferred toemploy the compounds (I) according to the invention in transgenic cropswhich are resistant to growth regulators such as, for example, dicamba,or to herbicides which inhibit essential plant enzymes, for exampleacetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS)or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from thegroup of the sulphonylureas, glyphosate, glufosinate orbenzoylisoxazoles and analogous active compounds.

On employment of the active compounds according to the invention intransgenic crops, not only do the effects toward harmful plants observedin other crops occur, but often also effects which are specific toapplication in the particular transgenic crop, for example an altered orspecifically widened spectrum of weeds which can be controlled, alteredapplication rates which can be used for the application, preferably goodcombinability with the herbicides to which the transgenic crop isresistant, and influencing of growth and yield of the transgenic cropplants.

The invention therefore also relates to the use of the compounds of theformula (I) according to the invention and/or their salts as herbicidesfor controlling harmful plants in crops of useful plants or ornamentals,optionally in transgenic crop plants.

Preference is given to the use by the pre- or post-emergence method incereals such as wheat, barley, rye, oats, millet and rice, in particularin wheat by the post-emergence method.

Preference is also given to the use by the pre- or post-emergence methodin maize, in particular by the pre-emergence method in maize.

Preference is also given to the use by the pre- or post-emergence methodin soybeans, in particular by the post-emergence method in soybeans.

The use according to the invention for the control of harmful plants orfor growth regulation of plants also includes the case in which theactive compound of the formula (I) or its salt is not formed from aprecursor substance (“prodrug”) until after application on the plant, inthe plant or in the soil.

The invention also provides the method (application method) forcontrolling harmful plants or for regulating the growth of plants whichcomprises applying an effective amount of one or more compounds of theformula (I) or salts thereof onto the plants (harmful plants, ifappropriate together with the useful plants), plant seeds, the soil inwhich or on which the plants grow or the area under cultivation.

The compounds (I) according to the invention can be used in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant-growth-regulatingcompositions which comprise compounds of the formula (I) and/or saltsthereof.

The compounds of the formula (I) and/or salts thereof can be formulatedin various ways according to which biological and/or physicochemicalparameters are required. Possible formulations include, for example:wettable powders (WP), water-soluble powders (SP), water-solubleconcentrates, emulsifiable concentrates (EC), emulsions (EW), such asoil-in-water and water-in-oil emulsions, sprayable solutions, suspensionconcentrates (SC), oil- or water-based dispersions, oil-misciblesolutions, capsule suspensions (CS), dusting products (DP),seed-dressing products, granules for broadcasting and soil application,granules (GR) in the form of microgranules, sprayable granules, coatedgranules and adsorption granules, water-dispersible granules (WG),water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Kuchler, “Chemische Technologie”[Chemical Technology], volume 7, C. Hanser Verlag Munich, 4th ed. 1986;Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd.London.

The necessary formulation aids, such as inert materials, surfactants,solvents and further additives are likewise known and are described, forexample, in: Watkins, “Handbook of Insecticide Dust Diluents andCarriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen,“Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons,N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963;McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active Ethylene OxideAdducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th ed.1986.

Wettable powders are preparations which can be dispersed uniformly inwater and, as well as the active compound, apart from a diluent or inertsubstance, also comprise surfactants of the ionic and/or nonionic type(wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulphates, alkanesulphonates,alkylbenzenesulphonates, sodium lignosulphonate, sodium2,2′-dinaphthylmethane-6,6′-disulphonate, sodiumdibutylnaphthalenesulphonate or else sodium oleoylmethyltaurinate. Toprepare the wettable powders, the herbicidally active compounds areground finely, for example in customary apparatus such as hammer mills,blower mills and air-jet mills, and simultaneously or subsequently mixedwith the formulation assistants.

Emulsifiable concentrates are produced by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with addition of oneor more surfactants of the ionic and/or nonionic type (emulsifiers).Emulsifiers used may, for example, be: alkylarylsulphonic acid calciumsalts, such as calcium dodecylbenzenesulphonate, or nonionic emulsifierssuch as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fattyalcohol polyglycol ethers, propylene oxide-ethylene oxide condensationproducts, alkyl polyethers, sorbitan esters, such as, for example,sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as,for example, polyoxyethylene sorbitan fatty acid esters.

Dusting products are obtained by grinding the active compound withfinely distributed solid substances, for example talc, natural clays,such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They can beproduced, for example, by wet grinding by means of commercial bead millswith optional addition of surfactants as already listed above, forexample, for the other formulation types. Emulsions, e.g. oil-in-wateremulsions (EW), can be prepared, for example, by means of stirrers,colloid mills and/or static mixers using aqueous organic solvents and ifappropriate surfactants, as have for example already been listed abovein connection with the other types of formulation.

Granules can be prepared either by spraying the active compound ontogranular inert material capable of adsorption or by applying activecompound concentrates to the surface of carrier substances, such assand, kaolinites or granular inert material, by means of adhesives, forexample polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitableactive ingredients can also be granulated in the manner customary forthe production of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are produced generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the production of pan granules, fluidized bed granules, extrudergranules and spray granules, see, for example, processes in“Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E.Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff.;“Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York1973, pp. 8-57.

For further details regarding the formulation of crop protection agents,see, for example, G. C. Klingman, “Weed Control as a Science”, JohnWiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S.A. Evans, “Weed Control Handbook”, 5th ed., Blackwell ScientificPublications, Oxford, 1968, pages 101-103.

The agrochemical preparations comprise generally from 0.1 to 99% byweight, in particular from 0.1 to 95% by weight, of active compound ofthe formula (I) and/or salts thereof.

In wettable powders, the active compound concentration is, for example,about 10 to 90% by weight; the remainder to 100% by weight consists ofcustomary formulation constituents. In the case of emulsifiableconcentrates, the active compound concentration can be from about 1 to90% by weight, preferably from 5 to 80% by weight. Dust-typeformulations contain from 1 to 30% by weight of active compound,preferably usually from 5 to 20% by weight of active compound; sprayablesolutions contain from about 0.05 to 80% by weight, preferably from 2 to50% by weight of active compound. In the case of water-dispersiblegranules, the active compound content depends partly on whether theactive compound is present in liquid or solid form and on whichgranulation assistants, fillers, etc., are used. In thewater-dispersible granules, the content of active compound is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary tackifiers, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity. Examplesof formulation auxiliaries are described, inter alia, in “Chemistry andTechnology of Agrochemical Formulations”, ed. D. A. Knowles, KluwerAcademic Publishers (1998).

The compounds of the formula (I) or salts thereof can be employed assuch or in the form of their preparations (formulations) combined withother pesticidally active compounds, such as, for example, insecticides,acaricides, nematicides, herbicides, fungicides, safeners, fertilizersand/or growth regulators, for example as finished formulation or as tankmixes. The combination formulations can be prepared on the basis of theabovementioned formulations, while taking account of the physicalproperties and stabilities of the active compounds to be combined.

Usable combination partners for the inventive compounds in mixtureformulations or in the tank mix are, for example, known activeingredients based on inhibition of, for example, acetolactate synthase,acetyl-CoA carboxylase, cellulose synthase,enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase,p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, photosystem I,photosystem II, protoporphyrinogen oxidase, as described, for example,in Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 15thedition, The British Crop Protection Council and the Royal Soc. ofChemistry, 2006 and literature cited therein. Known herbicides or plantgrowth regulators which can be combined with the compounds according tothe invention are, for example, the following active compounds (thecompounds are either designated by the common name according to theInternational Organization for Standardization (ISO) or by the chemicalname, or by the code number) and always comprise all use forms such asacids, salts, esters and isomers such as stereoisomers and opticalisomers. In this case, one or else, in some cases, more than one useform is mentioned by way of example: acetochlor, acibenzolar,acibenzolar-5-methyl, acifluorfen, acifluorfen-sodium, aclonifen,alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryne,amicarbazone, amidochlor, amidosulphuron, aminocyclopyrachlor,aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid,amitrole, ammonium sulphamate, ancymidol, anilofos, asulam, atrazine,azafenidin, azimsulphuron, aziprotryne, beflubutamid, benazolin,benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide,bensulphuron, bensulphuron-methyl, bentazone, benzfendizone,benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone,bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium,bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos,busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin,butroxydim, butylate, cafenstrole, carbetamide, carfentrazone,carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop,chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac,chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl,chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chloride,chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlortoluron,chlorsulphuron, cinidon, cinidon-ethyl, cinmethylin, cinosulphuron,clethodim, clodinafop, clodinafop-propargyl, clofencet,clofencet-potassium, clomazone, clomeprop, cloprop, clopyralid,cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine,cyclanilide, cycloate, cyclosulphamuron, cycloxydim, cycluron,cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D,2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol,desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba,dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron,difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium,dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn,dimethenamid, dimethenamid-P, dimethipin, dimetrasulphuron, dinitramine,dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide,dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb,ethalfluralin, ethametsulphuron, ethametsulphuron-methyl, ethephon,ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl,ethoxysulphuron, etobenzanid, F-5331, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulphonamide,F-7967, i.e.3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione,fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl,fenoxaprop-P-ethyl, fenoxasulphone, fentrazamide, fenuron, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulphuron, florasulam,fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate,flucarbazone, flucarbazone-sodium, flucetosulphuron, fluchloralin,flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn,fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,flupoxam, flupropacil, flupropanate, flupyrsulphuron,flupyrsulphuron-methyl-sodium, flurenol, flurenol-butyl, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol,flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen,foramsulphuron, forchlorfenuron, fosamine, furyloxyfen, gibberellicacid, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate,glyphosate-isopropylammonium, H-9201, i.e.O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate,halosafen, halosulphuron, halosulphuron-methyl, haloxyfop, haloxyfop-P,haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl,haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl(2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl,imazamox, imazamox-ammonium, imazapic, imazapyr,imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr,imazethapyr-ammonium, imazosulphuron, inabenfide, indanofan, indaziflam,indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulphuron,iodosulphuron-methyl-sodium, iofensulphuron, iofensulphuron-sodium,ioxynil, ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron,isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, i.e.3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulphonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole,karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide,MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium,mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium,mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide,mepiquat-chloride, mesosulphuron, mesosulphuron-methyl, mesotrione,methabenzthiazuron, metam, metamifop, metamitron, metazachlor,metazasulphuron, methazole, methiopyrsulphuron, methiozolin,methoxyphenone, methyldymron, 1-methylcyclopropene, methylisothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor,metosulam, metoxuron, metribuzin, metsulphuron, metsulphuron-methyl,molinate, monalide, monocarbamide, monocarbamide dihydrogensulphate,monolinuron, monosulphuron, monosulphuron ester, monuron, MT-128, i.e.6-chloro-N-[(2E)-3-chloroprop-2-en-1-yl]-5-methyl-N-phenylpyridazine-3-amine,MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide,NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulphuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium(isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,orthosulphamuron, oryzalin, oxadiargyl, oxadiazon, oxasulphuron,oxaziclomefone, oxyfluorfen, paclobutrazole, paraquat, paraquatdichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin,penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid,phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen,pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor,primisulphuron, primisulphuron-methyl, probenazole, profluazole,procyazine, prodiamine, prifluraline, profoxydim, prohexadione,prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propoxycarbazone-sodium, propyrisulphuron,propyzamide, prosulphalin, prosulphocarb, prosulphuron, prynachlor,pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulphotole, pyrazolynate(pyrazolate), pyrazosulphuron, pyrazosulphuron-ethyl, pyrazoxyfen,pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim,pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac,pyriminobac-methyl, pyrimisulphan, pyrithiobac, pyrithiobac-sodium,pyroxasulphone, pyroxsulam, quinclorac, quinmerac, quinoclamine,quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, rimsulphuron, saflufenacil, secbumeton,sethoxydim, siduron, simazine, simetryn, SN-106279, i.e. methyl(2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate,sulcotrione, sulphallate (CDEC), sulphentrazone, sulphometuron,sulphometuron-methyl, sulphosate (glyphosate-trimesium),sulphosulphuron, SW-065, SYN-523, SYP-249, i.e.1-ethoxy-3-methyl-1-oxobut-3-en-2-yl5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e.1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione,tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryne, thenylchlor, thiafluamide, thiazafluoron,thiazopyr, thidiazimin, thidiazuron, thiencarbazone,thiencarbazone-methyl, thifensulphuron, thifensulphuron-methyl,thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone,triallate, triasulphuron, triaziflam, triazofenamide, tribenuron,tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane,trietazine, trifloxysulphuron, trifloxysulphuron-sodium, trifluralin,triflusulphuron, triflusulphuron-methyl, trimeturon, trinexapac,trinexapac-ethyl, tritosulphuron, tsitodef, uniconazole, uniconazole-P,vernolate, ZJ-0862, i.e.3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, andthe following compounds:

Of particular interest is the selective control of harmful plants incrops of useful plants and ornamentals. Although the compounds (I)according to the invention have already demonstrated very good toadequate selectivity in a large number of crops, in principle, in somecrops and in particular also in the case of mixtures with other, lessselective herbicides, phytotoxicities on the crop plants may occur. Inthis connection, combinations of compounds (I) according to theinvention are of particular interest which comprise the compounds (I) ortheir combinations with other herbicides or pesticides and safeners. Thesafeners, which are used in an antidotically effective amount, reducethe phytotoxic side effects of the herbicides/pesticides employed, forexample in economically important crops, such as cereals (wheat, barley,rye, maize, rice, millet), sugar beet, sugar cane, oilseed rape, cottonand soybeans, preferably cereals. The following groups of compounds aresuitable, for example, as safeners for the compounds (I) and theircombinations with further pesticides:

A) Compounds of the Formula (S-I)

where the symbols and indices have the following meanings:

-   n_(A) is a natural number from 0 to 5, preferably from 0 to 3;-   R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or    (C₁-C₄)-haloalkyl;-   W_(A) is an unsubstituted or substituted divalent heterocyclic    radical from the group of the partially unsaturated or aromatic    five-membered heterocycles having 1 to 3 ring heteroatoms of the N    or O type, where at least one nitrogen atom and at most one oxygen    atom is present in the ring, preferably a radical from the group of    (W_(A) ¹) to (W_(A) ⁴),

-   m_(A) is 0 or 1;-   R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated or    unsaturated 3- to 7-membered heterocycle having at least one    nitrogen atom and up to 3 heteroatoms, preferably from the group of    O and S, which is joined to the carbonyl group in (S-I) via the    nitrogen atom and is unsubstituted or substituted by radicals from    the group of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or optionally substituted    phenyl, preferably a radical of the formula OR_(A) ³, NHR_(A) ⁴ or    N(CH₃)₂, especially of the formula OR_(A) ³;-   R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatic    hydrocarbon radical preferably having a total of 1 to 18 carbon    atoms;-   R_(A) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or    unsubstituted phenyl;-   R_(A) ⁵ is H, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,    (C₁-C₄)-alkoxy-(C₁-C₈)-alkyl, cyano or COOR_(A) ⁹ in which R_(A) ⁹    is hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl,    (C₃-C₁₂)-cycloalkyl or tri-(C₁-C₄)-alkylsilyl;-   R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different and are    hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₃-C₁₂)-cycloalkyl or    substituted or unsubstituted phenyl;    preferably:-   a) compounds of the type of the    dichlorophenylpyrazoline-3-carboxylic acid, preferably compounds    such as ethyl    1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate    (S1-1) (“mefenpyr-diethyl”, see Pestic. Man.), and related compounds    as described in WO 91/07874;-   b) derivatives of dichlorophenylpyrazolecarboxylic acid, preferably    compounds such as ethyl    1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl    1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3),    ethyl    1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate    (S1-4), ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate    (S1-5) and related compounds as described in EP-A-333 131 and    EP-A-269 806;-   c) compounds of the triazolecarboxylic acid type, preferably    compounds such as fenchlorazole(-ethyl), i.e. ethyl    1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate    (S1-6), and related compounds as described in EP-A-174 562 and    EP-A-346 620;-   d) compounds of the type of the 5-benzyl- or    5-phenyl-2-isoxazoline-3-carboxylic acid or the    5,5-diphenyl-2-isoxazoline-3-carboxylic acid, preferably compounds    such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate    (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and    related compounds, as described in WO 91/08202, or ethyl    5,5-diphenyl-2-isoxazolinecarboxylate (S1-9) (“isoxadifen-ethyl”) or    n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-10) or ethyl    5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-11), as    described in the patent application WO-A-95/07897.

B) Quinoline Derivatives of the Formula (S-II)

where the symbols and indices have the following meanings:

-   R_(B) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or    (C₁-C₄)-haloalkyl;-   n_(B) is a natural number from 0 to 5, preferably from 0 to 3;-   R_(B) ² is OR_(B) ³, SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated or    unsaturated 3- to 7-membered heterocycle having at least one    nitrogen atom and up to 3 heteroatoms, preferably from the group    consisting of O and S, which is joined to the carbonyl group in    (S-II) via the nitrogen atom and is unsubstituted or substituted by    radicals from the group of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or    optionally substituted phenyl, preferably a radical of the formula    OR_(B) ³, NHR_(B) ⁴ or N(CH₃)₂, especially of the formula OR_(B)3;-   R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatic    hydrocarbon radical preferably having a total of 1 to 18 carbon    atoms;-   R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or    unsubstituted phenyl;-   T_(B) is a (C₁ or C₂)-alkanediyl chain which is unsubstituted or    substituted by one or two (C₁-C₄)-alkyl radicals or by    [(C₁-C₃)-alkoxy]carbonyl;    preferably:-   a) compounds of the 8-quinolinoxyacetic acid type (S2), preferably-   1-methylhexyl 5-chloro-8-quinolinoxyacetate (common name    “cloquintocet-mexyl” (S2-1) (see Pestic. Man.),-   1,3-dimethylbut-1-yl 5-chloro-8-quinolinoxyacetate (S2-2),-   4-allyloxybutyl 5-chloro-8-quinolinoxyacetate (S2-3),-   1-allyloxyprop-2-yl 5-chloro-8-quinolinoxyacetate (S2-4),-   ethyl 5-chloro-8-quinolinoxyacetate (S2-5),-   methyl 5-chloro-8-quinolinoxyacetate (S2-6),-   allyl 5-chloro-8-quinolinoxyacetate (S2-7),-   2-(2-propylideneiminoxy)-1-ethyl 5-chloro-8-quinolinoxyacetate    (S2-8), 2-oxoprop-1-yl    -   5-chloro-8-quinolinoxyacetate (S2-9) and related compounds as        described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0        492 366, and also their hydrates and salts as described in        WO-A-2002/034048.-   b) compounds of the (5-chloro-8-quinolinoxy)malonic acid type,    preferably compounds such as diethyl    (5-chloro-8-quinolinoxy)malonate, diallyl    (5-chloro-8-quinolinoxy)malonate, methyl ethyl    (5-chloro-8-quinolinoxy)malonate and related compounds, as described    in EP-A-0 582 198.

C) Compounds of the Formula (S-III)

where the symbols and indices have the following meanings:

-   R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably dichloromethyl;-   R_(C) ², R_(C) ³ are identical or different and are hydrogen,    (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl,    (C₂-C₄)-haloalkenyl, (C₁-C₄)-alkylcarbamoyl-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenylcarbamoyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, dioxolanyl-(C₁-C₄)-alkyl, thiazolyl,    furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted    phenyl, or IV and IV together form a substituted or unsubstituted    heterocyclic ring,    -   preferably an oxazolidine, thiazolidine, piperidine, morpholine,    -   hexahydropyrimidine or benzoxazine ring;        preferably:    -   active compounds of the dichloroacetamide type which are        frequently used as    -   pre-emergence safeners (soil-active safeners), such as, for        example,-   “dichlormid” (see Pestic. Man.)    (═N,N-diallyl-2,2-dichloroacetamide),-   “R-29148” (=3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine from    Stauffer),-   “R-28725” (=3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine from    Stauffer),-   “benoxacor” (see Pestic. Man.)    (=4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine),-   “PPG-1292” (═N-allyl-N-[(1,3-dioxolan-2-Amethyl]dichloroacetamide    from PPG Industries),-   “DKA-24” (═N-allyl-N—[(allylaminocarbonyl)methyl]dichloroacetamide    from Sagro-Chem),-   “AD-67” or “MON 4660” (=3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane    from Nitrokemia or Monsanto),-   “T1-35” (=1-dichloroacetylazepane from TRI-Chemical RT)-   “diclonon” (dicyclonon) or “BAS145138” or “LAB145138”    (=3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane    from BASF) and-   “furilazole” or “MON 13900” (see Pestic. Man.)    (=(RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine).    D) N-Acylsulphonamides of the Formula (S-IIV) and their Salts

in which

-   R_(D) ¹ is hydrogen, a hydrocarbon radical, a hydrocarbonoxy    radical, a hydrocarbonthio radical or a heterocyclyl radical which    is preferably attached via a carbon atom, where each of the 4    last-mentioned radicals is unsubstituted or substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxy, carboxy, formyl, carboxamide,    sulphonamide and radicals of the formula —Z^(a)—R^(a), where each    hydrocarbon moiety has preferaby 1 to 20 carbon atoms and a    carbon-containing radical R_(D) ¹ including substituents has    preferably 1 to 30 carbon atoms;-   R_(D) ² is hydrogen or (C₁-C₄)-alkyl, preferably hydrogen, or-   R_(D) ¹ and R_(D) ² together with the group of the formula —CO—N—    are the radical of a 3- to 8-membered saturated or unsaturated ring;-   R_(D) ³ are identical or different and are halogen, cyano, nitro,    amino, hydroxy, carboxy, formyl, CONH₂, SO₂NH₂ or a radical of the    formula —Z^(b)—R^(b);-   R_(D) ⁴ is hydrogen or (C₁-C₄)-alkyl, preferably H;-   R_(D) ⁵ are identical or different and are halogen, cyano, nitro,    amino, hydroxy, carboxy, CHO, CONH₂, SO₂NH₂ or a radical of the    formula —Z^(c)—R^(c);-   R^(a) is a hydrocarbon radical or a heterocyclyl radical, where each    of the two last-mentioned radicals is unsubstituted or substituted    by one or more identical or different radicals from the group    consisting of halogen, cyano, nitro, amino, hydroxy, mono- and    di-[(C₁-C₄)-alkyl]amino, or an alkyl radical in which a plurality,    preferably 2 or 3, non-adjacent CH₂ groups are in each case replaced    by an oxygen atom;-   R^(b), R^(c) are identical or different and are a hydrocarbon    radical or a heterocyclyl radical, where each of the two    last-mentioned radicals is unsubstituted or substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxy, phosphoryl,    halo-(C₁-C₄)-alkoxy, mono- and di-[(C₁-C₄)-alkyl]amino, or an alkyl    radical in which a plurality, preferably 2 or 3, non-adjacent CH₂    groups are in each case replaced by an oxygen atom;-   Z^(a) is a divalent group of the formula —O—, —S—, —CO—, —CS—,    —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO₂—, —NR*—, —CO—NR*—,    —NR*—CO—, —SO₂—NR*— or —NR*—SO₂—, where the bond indicated on the    right-hand side of the divalent group in question is the bond to the    radical R^(a) and where the R* in the 5 last-mentioned radicals    independently of one another are each H, (C₁-C₄)-alkyl or    halo-(C₁-C₄)-alkyl;-   Z^(b),Z^(c) are independently of one another a direct bond or a    divalent group of the formula —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—,    —O—CO—, —S—CO—, —SO—, —SO₂—, —NR*—, —SO₂—NR*—, —NR*—SO₂—, —CO—NR*—    or —NR*—CO—, where the bond indicated on the right-hand side of the    divalent group in question is the bond to the radical R^(b) or R^(c)    and where the R* in the 5 last-mentioned radicals independently of    one another are each H, (C₁-C₄)-alkyl or halo-(C₁-C₄)-alkyl;-   n_(D) is an integer from 0 to 4, preferably 0, 1 or 2, particularly    preferably 0 or 1, and-   m_(D) is an integer from 0 to 5, preferably 0, 1, 2 or 3, in    particular 0, 1 or 2.

E) Acylsulphamoylbenzamides of the General Formula (S-V), if AppropriateAlso in Salt Form,

in which

-   X_(E) is CH or N,-   R_(E) ¹ is hydrogen, heterocyclyl or a hydrocarbon radical, where    the two last-mentioned radicals are optionally substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH₂, SO₂NH₂    and Z^(a)—R^(a);-   R_(E) ² is hydrogen, hydroxy, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, where the five    last-mentioned radicals are optionally substituted by one or more    identical or different radicals from the group consisting of    halogen, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and    (C₁-C₄)-alkylthio, or-   R_(E) ¹ and R_(E) ² together with the nitrogen atom that carries    them are a 3- to 8-membered saturated or unsaturated ring;-   R_(E) ³ is halogen, cyano, nitro, amino, hydroxy, carboxy, CHO,    CONH₂, SO₂NH₂ or Z^(b)—R^(b);-   R_(E) ⁴ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or    (C₂-C₄)-alkynyl;-   R_(E) ⁵ is halogen, cyano, nitro, amino, hydroxy, carboxy,    phosphoryl, CHO, CONH₂, SO₂NH₂ or Z^(c)—R^(c);-   R^(a) is a (C₂-C₂₀)-alkyl radical whose carbon chain is interrupted    once or more than once by oxygen atoms, is heterocyclyl or a    hydrocarbon radical, where the two last-mentioned radicals are    optionally substituted by one or more identical or different    radicals from the group consisting of halogen, cyano, nitro, amino,    hydroxy, mono- and di-[(C₁-C₄)-alkyl]-amino;-   R^(b), R^(c) are identical or different and are a (C₂-C₂₀)-alkyl    radical whose carbon chain is interrupted once or more than once by    oxygen atoms, are heterocyclyl or a hydrocarbon radical, where the    two last-mentioned radicals are optionally substituted by one or    more identical or different radicals from the group consisting of    halogen, cyano, nitro, amino, hydroxy, phosphoryl,    (C₁-C₄)-haloalkoxy, mono- and di-[(C₁-C₄)-alkyl]amino; Za is a    divalent unit from the group consisting of O, S, CO, CS, C(O)O,    C(O)S, SO, SO₂, NR^(d), C(O)NR^(d) and SO₂NR^(d);-   Z^(b), Z^(c) are identical or different and are a direct bond or a    divalent unit from the group consisting of O, S, CO, CS, C(O)O,    C(O)S, SO, SO₂, NR^(d), SO₂NR^(d) and C(O)NR^(d);-   R^(d) is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-haloalkyl;-   n_(E) is an integer from 0 to 4, and-   m_(E) if X is CH, is an integer from 0 to 5, and, if X is N, is an    integer from 0 to 4;    -   from among these, preference is given to compounds (also in the        form of their salts) of the type of the        acylsulphamoylbenzamides, for example of the formula (S-VI)        below, which are known, for example, from WO 99/16744,

-   -   for example those in which    -   R_(E) ¹=cyclopropyl and R_(E) ⁵=2-OMe (“cyprosulphamide”, S3-1),    -   R_(E) ¹=cyclopropyl and R_(E) ⁵=5-Cl-2-OMe (S3-2),    -   R_(E) ¹=ethyl and R_(E) ⁵=2-OMe (S3-3),    -   R_(E) ¹=isopropyl and R_(E) ⁵=5-Cl-2-OMe (S3-4) and    -   R_(E) ¹⁼isopropyl and R_(E) ⁵=2-OMe (S3-5);        F) Compounds of the Type of the N-Acylsulphamoylphenylureas of        the Formula (S-VII), which are Known, for Example, from        EP-a-365484

in which

-   A is a radical from the group consisting of

-   R_(F) ¹ and R_(F) ² independently of one another are hydrogen,    (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₆)-alkenyl, (C₃-C₆)-alkynyl,

or (C₁-C₄)-alkoxy substituted by

or (C₁-C₄)-akoxy, or

-   R_(F) ¹ and R_(F) ² together are a (C₄-C₆)-alkylene bridge or a    (C₄-C₆)-alkylene bridge interrupted by oxygen, sulphur, SO, SO₂, NH    or —N(C₁-C₄-alkyl)-,-   R_(F) ³ is hydrogen or (C₁-C₄)-alkyl,-   R_(F) ⁴ and R_(F) ⁵ independently of one another are hydrogen,    halogen, cyano, nitro, trifluoromethyl, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulphinyl, C₁-C₄-alkylsulphonyl,    —COOR^(j), —CONR^(k)R^(m), —COR^(n), —SO₂NR^(k)R^(m) or    —OSO₂—C₁-C₄-alkyl, or R^(a) and R^(b) together are a    (C₃-C₄)-alkylene bridge which may be substituted by halogen or    C₁-C₄-alkyl, or a (C₃-C₄)-alkenylene bridge which may be substituted    by halogen or (C₁-C₄)-alkyl, or a C₄-alkadienylene bridge which may    be substituted by halogen or (C₁-C₄)-alkyl, and-   R^(g) and R^(h) independently of one another are hydrogen, halogen,    C₁-C₄-alkyl, trifluoromethyl, methoxy, methylthio or —COOR^(j),    where-   R^(c) is hydrogen, halogen, (C₁-C₄)-alkyl or methoxy,-   R^(d) is hydrogen, halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl, (C₁-C₄)-alkylsulphonyl,    —COOR^(j) or —CONR^(k)R^(m),-   R^(e) is hydrogen, halogen, C₁-C₄-alkyl, —COOR^(j), trifluoromethyl    or methoxy, or R^(d) and R^(e) together are a (C₃-C₄)-alkylene    bridge,-   R^(f) is hydrogen, halogen or (C₁-C₄)-alkyl,-   R^(X) and R^(Y) independently of one another are hydrogen, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylthio, —COOR⁴,    trifluoromethyl, nitro or cyano,-   R^(j), R^(k) and R^(m) independently of one another are hydrogen or    (C₁-C₄)-alkyl, R^(k) and R^(m) together are a (C₄-C₆)-alkylene    bridge or a (C₄-C₆)-alkylene bridge interrupted by oxygen, NH or    —N(C₁-C₄-alkyl)-, and-   R^(n) is (C₁-C₄)-alkyl, phenyl or phenyl substituted by halogen,    (C₁-C₄)-alkyl, methoxy, nitro or trifluoromethyl,    from among these, preference is given to:-   1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea,-   1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea,-   1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea,-   1-[4-(N-naphthoylsulphamoyl)phenyl]-3,3-dimethylurea, including the    stereoisomers and agriculturally customary salts,-   G) active compounds from the class of the hydroxyaromatics and the    aromatic-aliphatic carboxylic acid derivatives, for example ethyl    3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid,    3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid,    4-fluorosalicylic acid,    1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide,    2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in    WO 2004084631, WO 2005015994, WO 2006007981, WO 2005016001;-   H) active compounds from the class of the    1,2-dihydroquinoxalin-2-ones, for example    -   1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,        1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,        1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one        hydrochloride,        1-(2-methylsulphonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,        as described in WO 2005112630,-   I) active compounds which, in addition to herbicidal action against    harmful plants, also have safener action on crop plants such as    rice, for example    -   “dimepiperate” or “MY-93” (see Pestic. Man.)        (═S-1-methyl-1-phenylethyl piperidine-1-thiocarboxylate), which        is known as safener for rice against damage caused by the        herbicide molinate,    -   “daimuron” or “SK 23” (see Pestic. Man.)        (=1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as        safener for rice against imazosulphuron herbicide damage,    -   “cumyluron”=“JC-940”        (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethypurea, see        JP-A-60087254), which is known as safener for rice against        damage by some herbicides,    -   “methoxyphenone” or “NK 049”        (=3,3′-dimethyl-4-methoxybenzophenone), which is known as        safener for rice against damage by some herbicides, “CSB”        (=1-bromo-4-(chloromethylsulphonyl)benzene) (CAS Reg. No.        54091-06-4 from Kumiai), which is known as safener for rice        against damage by some herbicides,-   K) compounds of the formula (S-IX), as described in WO-A-1998/38856,

-   -   where the symbols and indices have the following meanings:    -   R_(K) ¹, R_(K) ² independently of one another are halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, nitro;    -   A_(K) is COOR_(K) ³ or COOR_(K) ⁴    -   R_(K) ³, R_(K) ⁴ independently of one another are hydrogen,        (C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl,        (C₁-C₄)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl,        pyridinylalkyl and alkylammonium,    -   n_(K) ¹ is 0 or 1 and    -   n_(K) ², n_(K) ³ independently of one another are 0, 1 or 2;        preferably:        methyl (diphenylmethoxy)acetate (CAS reg no: 41858-19-9),

-   L) compounds of the formula (S-X)    -   as described in WO A-98/27049

where the symbols and indices have the following meanings:

-   X_(L) is CH or N,-   n_(L) if X═N, is an integer from 0 to 4 and if X═CH, is an integer    from 0 to 5,-   R_(L) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl, optionally    substituted phenyl, optionally substituted phenoxy,-   R_(L) ² is hydrogen or (C₁-C₄)-alkyl-   R_(L) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-alkynyl, or aryl, where each of the aforementioned    carbon-containing radicals is unsubstituted or substituted by one or    more, preferably up to three identical or different radicals from    the group consisting of halogen and alkoxy; or salts thereof.-   M) Active compounds from the class of the    3-(5-tetrazolylcarbonyl)-2-quinolones, for example    1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone    (CAS Reg. No.: 219479-18-2),    1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone    (CAS Reg. No.: 95855-00-8), as described in WO-A-1999000020,-   N) compounds of the formula (S-XI) or (S-XII) as described in    WO-A-2007023719 and WO-A-2007023764

-   -   in which

-   R_(N) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃, OCF₃,

-   Y, Z independently of one another are O or S,

-   n_(N) is an integer from 0 to 4,

-   R_(N) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,    aryl; benzyl, halobenzyl,

-   R_(N) ³ is hydrogen, (C₁-C₆)-alkyl;

-   O) one or more compounds from the group consisting of:

-   1,8-naphthalic anhydride,

-   O,O -diethyl S-2-ethylthioethyl phosphorodithioate (disulfoton),

-   4-chlorophenyl methylcarbamate (mephenate),

-   O,O -diethyl O-phenyl phosphorothioate (dietholate),

-   4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS    Reg. No.: 31541-57-8),

-   2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate (MG-838, CAS    Reg. No.: 133993-74-5),

-   methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate    (from WO-A-98/13361; CAS Reg. No.: 205121-04-6),

-   cyanomethoxyimino(phenyl)acetonitrile (cyometrinil)

-   1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil),

-   4′-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime    (fluxofenim),

-   4,6-dichloro-2-phenylpyrimidine (fenclorim),

-   benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate    (flurazole),

-   2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),    -   including the stereoisomers possible in each case, and the salts        customary in agriculture.

The weight ratios of herbicide (mixture) to safener depend generally onthe herbicide application rate and the efficacy of the safener inquestion and may vary within wide limits, for example in the range from200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20.Analogously to the compounds (I) or mixtures thereof, the safeners canbe formulated with further herbicides/pesticides and be provided andemployed as a finished formulation or tank mix with the herbicides.

For application, the herbicide or herbicide/safener formulations presentin commercial form are, if appropriate, diluted in a customary manner,for example in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules with water. Preparations inthe form of dusts, granules for soil application or granules forbroadcasting and sprayable solutions are usually no longer diluted withother inert substances prior to application.

The required application rate of the compounds of the formula (I) and/ortheir salts varies according to the external conditions such as, interalia, temperature, humidity and the type of herbicide used. It can varywithin wide limits. For the application as herbicide for controllingharmful plants, it is, for example, in the range of from 0.001 to 10.0kg/ha or more of active substance, preferably in the range of from 0.005to 5 kg/ha, in particular in the range of from 0.01 to 1 kg/ha, ofactive substance. This applies both to the pre-emergence and thepost-emergence application.

When used as plant growth regulator, for example as culm stabilizer forcrop plants like those mentioned above, preferably cereal plants, suchas wheat, barley, rye, triticale, millet, rice or maize, the applicationrate is, for example, in the range of from 0.001 to 2 kg/ha or more ofactive substance, preferably in the range of from 0.005 to 1 kg/ha, inparticular in the range of from 10 to 500 g/ha of active substance, veryparticularly from 20 to 250 g/ha of active substance (please checkwhether this should be stated). This applies both to application by thepre-emergence method and the post-emergence method, the post-emergencetreatment generally being preferred. The application as culm stabilizermay take place at various stages of the growth of the plants. Preferredis, for example, the application after the tillering phase, at thebeginning of the longitudinal growth.

As an alternative, application as plant growth regulator is alsopossible by treating the seed, which includes various techniques fordressing and coating seed. Here, the application rate depends on theparticular techniques and can be determined in preliminary tests.

In an exemplary manner, some synthesis examples of compounds of thegeneral formula (I) are described below. In the examples, the amounts(including percentages) refer to the weight, unless especially statedotherwise. The symbols “>” and “<” mean “greater than” and “smallerthan”, respectively. The symbol “≧” means “greater than or equal to”,the symbol “≦” means “smaller than or equal to”.

If, in the context of the description and the examples, the terms “R”and “S” are given for the absolute configuration on a centre ofchirality of the stereoisomers of the formula (I), this RS nomenclaturefollows, unless defined differently, the Cahn-Ingold-Prelog rule.

(A) SYNTHESIS EXAMPLES Example A1 Erythro- and threo-Methyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate (Table 2, Exampleserythro-Ibb5 and threo-Ibb5)

Under protective gas (Ar), 0.1 ml of 30% strength methanolic sodiummethoxide solution was added to 1.200 g (6.810 mmol) of methyl3-(4-methylphenyl)acrylate and 0.805 g (6.810 mmol) ofpyridin-3-ylacetonitrile in 6.0 ml of methanol, and the mixture wasstirred at 50° C. for 24 h. The reaction mixture was poured intoice-water and extracted three times with ethyl acetate, and the combinedorganic phases were dried over sodium sulphate. The solvent was removedunder reduced pressure. Chromatography of the residue on silica gel(ethyl acetate/heptane=85:15) gave, successively, 0.361 g (16% oftheory) of threo-methyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate and 0.427 g (19% oftheory) of erythro-methyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate. The configurationwas assigned by comparison of the chemical shifts of the respective CHCNdoublets at 4.13 ppm and 4.44 ppm, respectively, in the ¹H-NMR (CDCl₃).The lower-field signal was assigned to the erythro-diastereomer,analogously to the literature. ¹H-NMR in CDCl₃ see Table 2.

Example A2 Erythro- and threo- Ethyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate (Table 2, Exampleserythro-Ibc5 and threo-Ibc5)

Under protective gas (Ar), 0.1 ml of 30% strength methanolic sodiummethoxide solution was added to 1.000 g (5.257 mmol) of ethyl3-(4-methylphenyl)acrylate and 0.621 g (5.257 mmol) ofpyridin-3-ylacetonitrile in 12.0 ml of ethanol, and the mixture wasstirred in a closed reaction vessel in a microwave oven at 90° C. for 3h. The reaction mixture was poured into ice-water and extracted threetimes with ethyl acetate, and the combined organic phases were driedover sodium sulphate. The solvent was removed under reduced pressure.Chromatography of the residue on silica gel (ethylacetate/heptane=70:30) gave, successively, 0.358 g (20% of theory) ofthreo-ethyl 4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate and0.320 g (18% of theory) of erythro-ethyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate. The configurationwas assigned by comparison of the chemical shifts of the respective CHCNdoublets at 4.12 ppm and 4.43 ppm, respectively, in the ¹H-NMR (CDCl₃).The lower-field signal was assigned to the erythro-diastereomer,analogously to the literature. ¹H-NMR in CDCl₃ see Table 2.

Example A3 Erythro- and threo-methyl4-cyano-4-(pyridin-3-yl)-3-(4-bromophenyl)butanoate (Table 2, Exampleserythro-Ibb3 and threo-Ibb3)

Under protective gas (Ar), 0.24 ml of 30% strength methanolic sodiummethoxide solution was added to 2.400 g (9.955 mmol) of methyl3-(4-bromophenyl)acrylate and 1.176 g (9.955 mmol) ofpyridin-3-ylacetonitrile in 28.8 ml of methanol, and the mixture wasstirred in a closed reaction vessel in a microwave oven at 110° C. for 4h. The reaction mixture was poured into ice-water and extracted threetimes with dichloromethane, and the combined organic phases were driedover sodium sulphate. The solvent was removed under reduced pressure.Chromatography of the residue on silica gel (ethylacetate/heptane=80:10) gave, successively, 0.653 g (16% of theory) ofthreo-methyl 4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate and0.986 g (25% of theory) of erythro-methyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate. The configurationwas assigned by comparison of the chemical shifts of the respective CHCNdoublets at 4.15 ppm and 4.48 ppm, respectively, in the ¹H-NMR (CDCl₃).The lower-field signal was assigned to the erythro-diastereomer,analogously to the literature. ¹H-NMR in CDCl₃ see Table 2.

Example A4 (3S,4S)-Methyl4-cyano-4-(pyridin-3-yl)-3-(4-bromophenyl)butanoate (Table 2, Examplethreo-1-Ibb3)

Preparative chromatography [(90 ml/min of n-heptane/2-propanol (50:50)]of the mixture, obtained in Example A3, of the racemic threo-methyl4-cyano-4-(pyridin-3-yl)-3-(4-bromophenyl)butanoate on a chiral solidphase [Chiralpak IC, 20 μm, (250×50)-mm column] gave 0.194 g of(3S,4S)-methyl 4-cyano-4-(pyridin-3-yl)-3-(4-bromophenyl)butanoate[chemical purity >95% (NMR), isomeric purity >99% (chiral HPLC)], whichwas the first of the two stereoisomers to elute (retention time=11.98min). For ¹H-NMR in CDCl₃ and retention time in analytical HPLC: seeTable 2.

Example A5 (3R,4R)-Methyl4-cyano-4-(pyridin-3-yl)-3-(4-bromophenyl)butanoate (Table 2, Examplethreo-2-Ibb3)

Preparative chromatography [(90 ml/min of n-heptane/2-propanol (50:50)]of the mixture, obtained in Example A3, of the racemic threo-methyl4-cyano-4-(pyridin-3-yl)-3-(4-bromophenyl)butanoate on a chiral solidphase [Chiralpak IC, 20 μm, (250×50)-mm column] gave 0.203 g of(3R,4R)-methyl 4-cyano-4-(pyridin-3-yl)-3-(4-bromophenyl)butanoate[chemical purity >95% (NMR), isomeric purity >99% (chiral HPLC)], whichwas the last of the two stereoisomers to elute (retention time=24.97min). For ¹H-NMR in CDCl₃ and retention time in analytical HPLC: seeTable 2.

The compounds, described in the tables below, of the absoluteconfiguration (3S,4S) and (3R,4R) are obtained according to oranalogously to the examples described above.

Example A6 4-Cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoic acid(Table 2, Example Iba5)

Under protective gas (Ar), 2.0 ml of 2 molar aqueous sodium hydroxidesolution were added to 0.300 g (1.019 mmol) of erythro-methyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate (Example A1) in10.0 ml of methanol, and the mixture was stirred at 25° C. for 8 h. Themethanol was removed under reduced pressure. The residue was acidifiedwith 2N aqueous hydrochloric acid (pH=3-4). Filtration and drying underhigh vacuum at 40° C. of the solid formed gave 0.178 g (56% of theory)of the title compound as a colourless solid [(erythro:threo=62:38,comparison of the doublets in the ¹H-NMR in [D₆]-DMSO at 4.65 (threo)and 4.71 ppm (erythro)]. Melting point 185-187° C. ¹H-NMR in [D₆]-DMSOsee Table 2.

Example A7 Erythro- and threo-2-(Phenylsulphanyl)ethyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate (Table 2, Exampleserythro-Ibv5 and threo-Ibv5)

Under protective gas (Ar), 0.176 g (0.920 mmol) ofN′—(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, a spatulatip of 4-dimethylaminopyridine (DMAP) and 0.296 g (1.917 mmol) of2-(phenylsulphanyl)ethanol were added to 0.215 g (0.767 mmol) of4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoic acid (Example A6) in2.7 ml of dichloromethane, and the mixture was stirred at 25° C. for 6h. Water was added to the reaction mixture and the aqueous phase wasextracted twice with dichloromethane. The combined organic phases weredried over sodium sulphate and the solvent was removed under reducedpressure. Chromatography of the residue on silica gel (gradient:starting with ethyl acetate/heptane=10:90 over 50 minutes to ethylacetate/heptane=90:10) gave, successively, 0.052 g (16% of theory) ofthreo-2-(phenylsulphanyl)ethyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate and 0.069 g (22% oftheory) of erythro-2-(phenylsulphanyl)ethyl4-cyano-4-(pyridin-3-yl)-3-(4-methylphenyl)butanoate. The configurationwas assigned by comparison of the chemical shifts of the respective CHCNdoublets at 4.11 ppm and 4.42 ppm, respectively, in the ¹H-NMR (CDCl₃).The lower-field signal was assigned to the erythro-diastereomer,analogously to the literature. ¹H-NMR in CDCl₃ see Table 2.

The compounds described in the table below are obtained according to oranalogously to the examples described above.

In the tables:

-   Ex.=Example number-   H=hydrogen (atom)-   Me=methyl-   Et=ethyl-   n-Pr=n-propyl-   i-Pr=isopropyl-   rt=retention time-   F, Cl, Br, I=fluorine, chlorine, bromine and iodine, respectively,    in accordance with the conventional chemical atom symbols-   CN=cyano-   NO₂=nitro-   MeO or OMe=methoxy-   CF₃=trifluoromethyl-   OCF₃=trifluoromethoxy-   OCF₂H=difluoromethoxy-   CO₂Me=methoxycarbonyl (“methylester group”)-   CO₂H=hydroxycarbonyl (“acid group”)

The position of a substituent at the phenyl ring, for example inposition 2, is stated as a prefix to the symbol or the abbreviation ofthe radical, for example

-   2-Cl=2-chloro-   2-F=2-fluoro

Numerations of the substituent positions for di- or trisubstitutedsubstitution patterns are analogously stated as a prefix, for example

-   3,4-Me₂=3,4-dimethyl (e.g. as substitution at the phenyl ring)-   3,5-F₂=3,5-difluoro (e.g. as substitution at the phenyl ring)-   3,4-F₂=3,4-difluoro (e.g. as substitution at the phenyl ring)

In addition, the customary chemical symbols and formulae apply, such as,for example, CH₂ for methylene or CF₃ for trifluoromethyl or OH forhydroxyl. Correspondingly, composite meanings are defined as composed ofthe abbreviations mentioned.

The retention times (“rt”) given for the compounds of Tables 2a-2f wereobtained by analytical HPLC of the compounds (I) on a chiral solidphase. At a concentration of 1 mg/ml, the compounds of the formula (I)were dissolved in dichloromethane p.a. and directly subjected to HPLC.The chromatographically purified compounds (I) have a stereochemicalpurity of ≧90%.

TABLE 1 Definitions of the radicals (R²)_(n) for the compounds of thegeneral formula (I) according to the invention mentioned in the tablesbelow No. (R²)n 1 4-F 2 4-Cl 3 4-Br 4 4-I 5 4-Me 6 4-CN 7 4-NO₂ 8 4-OMe9 4-i-Pr 10 4-CO₂Me 11 4-CO₂H 12 4-CF₃ 13 4-OCF₃ 14 3-F 15 3-Cl 16 3-Br17 3-Me 18 3-CN 19 3-NO₂ 20 3-OMe 21 3-CF₃ 22 3-OCF₃ 23 2-F 24 2-Cl 252-Br 26 2-Me 27 2-CN 28 2-NO₂ 29 2-OMe 30 2-CF₃ 31 2-OCF₃ 32 2,3-F₂ 332,4-F₂ 34 2,5-F₂ 35 2,6-F₂ 36 3,4-F₂ 37 3,5-F₂ 38 3,4,5-F₃ 39 2,3-Cl₂ 402,4-Cl₂ 41 2,5-Cl₂ 42 2,6-Cl₂ 43 3,4-Cl₂ 44 3,5-Cl₂ 45 2-F, 3-Cl 46 2-F,4-Cl 47 2-F, 5-Cl 48 2-Cl, 6-F 49 2,6-F₂, 4-Cl 50 3-F, 4-Cl 51 3-F, 4-Br52 3-F, 4-CN 53 3-F, 4-NO₂ 54 3-F, 4-OMe 55 3-Cl, 4-F 56 3-Cl, 5-F 572-Cl, 3-F 58 2-Cl, 4-F 59 2-Cl, 5-F 60 2-F, 4-Br 61 3-CN, 4-F 62 3-NO₂,4-F 63 3-CN, 4-Cl 64 3-NO₂, 4-Cl 65 2,6-(CN)₂ 66 2,5-(CN)₂ 67 2-CN, 5-F68 2-CN, 6-F 69 2-F, 5-CN 70 2,6-(NO₂)₂ 71 2,5-(NO₂)₂ 72 2-NO₂, 5-F 732-NO₂, 6-F 74 2-F, 5-NO₂ 75 3-CN, 4-F

Definition of the examples in Tables 2 to 2f below:

For reference purposes, specific numbers (=Example Numbers) have beenassigned to the individual compounds in Tables 2 to 2f below, where theExample Number in question is composed of the number of the chemicalformula assigned to the respective table and a “row number” (row number)which refers to the same number in the row of the first column ofTable 1. The chemical structure of Example No. “(formula number) (rownumber)” is thus defined unambiguously by the formula above therespective table according to formula number and row number of Table 1,for example:

The example of No. “Iba1” from Table 2 is the compound of the formula(Ib) in which R¹═H (=hydrogen) [=formula (Iba)] and (R²)_(n)=4-F,defined according to row 1 of Table 1.

The example of No. “Ibd18” from Table 2 is the compound of the formula(Ib) in which R¹=n-propyl [=formula (Ibd)] and (R²)_(n)=3-CN, definedaccording to row 18 of Table

This applies correspondingly to the assignment of racemic or opticallyactive threo stereoisomers or erythro stereoisomers. For example, forreference purposes, specific numbers (=Example Numbers) have beenassigned to the compounds of Table 2a, where the number “threo-Iba(rownumber)” refers to the racemic mixture of the threo enantiomers havingthe chemical structure of the formulae (S-lba) and (threo-2-Iba), eachof which has the meaning of group (R²)_(n) according to the row numberof Table 1.

TABLE 2 Compounds of the formulae (Ib), (Iba), (Ibb), (Ibc), (Ibd),(Ibe), (Ibf), (Ibg), (Ibh), (Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn),(Ibo), (Ibp), (Ibq), (Ibr), (Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx),(Iby) and (Ibz) where (R²)_(n) are as defined in Table 1 (Ib)

For definitions of subformulae of formula (Ib), see Table U1 below:

TABLE U1 Formula Radical R¹ in formula (Ib) (Iba) H (hydrogen atom)(Ibb) methyl (Ibc) ethyl (Ibd) n-propyl (Ibe) isopropyl (Ibf)2,2-difluoroethyl (Ibg) 2,2,2-trifluoroethyl (Ibh) 2-methoxyethyl (Ibi)cyclopropylmethyl (Ibj) (1-methylcyclopropyl)methyl (Ibk) allyl (Ibl)prop-2-yn-1-yl (Ibm) ethynyl (Ibn) prop-1-yn-1-yl (Ibo) benzyl (Ibp)4-chlorobenzyl (Ibq) phenyl (Ibr) methoxymethyl (Ibs) difluoromethyl(Ibt) oxetan-3-yl (Ibu) thietan-3-yl (Ibv) 2-(phenylsulphanyl)ethyl(Ibw) 2-(phenylsulphinyl)ethyl (Ibx) 2-(ethylsulphanyl)ethyl (Iby)2-(ethylsulphinyl)ethyl (Ibz) tetrahydrofuran-2-ylmethyl

Erythro/threo mixtures of the formulae (Iba) to (Ibz):

Examples of compounds of the formulae (Iba) to (Ibz) are the compoundsof the respective formulae (Iba) to (Ibz), in each case in the form of aracemic erythro/threo mixture (ratio 70:30 to 30:70), where the meaningof group (R²)_(n) is defined according to a row number of Table 1.

The numeration is carried out according to “(formula) (row number)”without any brackets, for example Iba50=compound of the formula (Iba)with (R²)_(n) according to row 50 of Table 1.

Tables 2a, 2b and 2c:

Threo, threo-1 and threo-2 compounds for the compounds of the formulae(Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe), (Ibf), (Ibg), (Ibh), (Ibi),(Ibj), (Ibk), (Ibl), (Ibm), (Ibn), (Ibo), (Ibp), (Ibq), (Ibr), (Ibs),(Ibt), (Ibu), (Ibv), (Ibw), (Ibx), (Iby) and (Ibz), where group (R²)_(n)is as defined in Table 1

For definitions of subformulae of formulae (threo-Ib), (threo-1-Ib) and(threo-2-Ib), see Table U2 below:

TABLE U2 Formula Radical R¹ in formula (threo-Ib) (threo-Iba) H(hydrogen atom) (threo-1-Iba) H (hydrogen atom) (threo-2-Iba) H(hydrogen atom) (threo-Ibb) methyl (threo-1-Ibb) methyl (threo-2-Ibb)methyl (threo-Ibc) ethyl (threo-1-Ibc) ethyl (threo-2-Ibc) ethyl(threo-Ibd) n-propyl (threo-1-Ibd) n-propyl (threo-2-Ibd) n-propyl(threo-Ibe) isopropyl (threo-1-Ibe) isopropyl (threo-2-Ibe) isopropyl(threo-Ibf) 2,2-difluoroethyl (threo-1-Ibf) 2,2-difluoroethyl(threo-2-Ibf) 2,2-difluoroethyl (threo-Ibg) 2,2,2-trifluoroethyl(threo-1-Ibg) 2,2,2-trifluoroethyl (threo-2-Ibg) 2,2,2-trifluoroethyl(threo-Ibh) 2-methoxyethyl (threo-1-Ibh) 2-methoxyethyl (threo-2-Ibh)2-methoxyethyl (threo-Ibi) cyclopropylmethyl (threo-1-Ibi)cyclopropylmethyl (threo-2-Ibi) cyclopropylmethyl (threo-Ibj)(1-methylcyclopropyl)methyl (threo-1-Ibj) (1-methylcyclopropyl)methyl(threo-2-Ibj) (1-methylcyclopropyl)methyl (threo-Ibk) allyl(threo-1-Ibk) allyl (threo-2-Ibk) allyl (threo-Ibl) prop-2-yn-1-yl(threo-1-Ibl) prop-2-yn-1-yl (threo-2-Ibl) prop-2-yn-1-yl (threo-Ibm)ethynyl (threo-1-Ibm) ethynyl (threo-2-Ibm) ethynyl (threo-Ibn)prop-1-yn-1-yl (threo-1-Ibn) prop-1-yn-1-yl (threo-2-Ibn) prop-1-yn-1-yl(threo-Ibo) benzyl (threo-1-Ibo) benzyl (threo-2-Ibo) benzyl (threo-Ibp)4-chlorobenzyl (threo-1-Ibp) 4-chlorobenzyl (threo-2-Ibp) 4-chlorobenzyl(threo-Ibq) phenyl (threo-1-Ibq) phenyl (threo-2-Ibq) phenyl (threo-Ibr)methoxymethyl (threo-1-Ibr) methoxymethyl (threo-2-Ibr) methoxymethyl(threo-Ibs) difluoromethyl (threo-1-Ibs) difluoromethyl (threo-2-Ibs)difluoromethyl (threo-Ibt) oxetan-3-yl (threo-1-Ibt) oxetan-3-yl(threo-2-Ibt) oxetan-3-yl (threo-Ibu) thietan-3-yl (threo-1-Ibu)thietan-3-yl (threo-2-Ibu) thietan-3-yl (threo-Ibv)2-(phenylsulphanyl)ethyl (threo-1-Ibv) 2-(phenylsulphanyl)ethyl(threo-2-Ibv) 2-(phenylsulphanyl)ethyl (threo-Ibw)2-(phenylsulphinyl)ethyl (threo-1-Ibw) 2-(phenylsulphinyl)ethyl(threo-2-Ibw) 2-(phenylsulphinyl)ethyl (threo-Ibx)2-(ethylsulphanyl)ethyl (threo-1-Ibx) 2-(ethylsulphanyl)ethyl(threo-2-Ibx) 2-(ethylsulphanyl)ethyl (threo-Iby)2-(ethylsulphinyl)ethyl (threo-1-Iby) 2-(ethylsulphinyl)ethyl(threo-2-Iby) 2-(ethylsulphinyl)ethyl (threo-Ibz)tetrahydrofuran-2-ylmethyl (threo-1-Ibz) tetrahydrofuran-2-ylmethyl(threo-2-Ibz) tetrahydrofuran-2-ylmethyl

Table 2a (threo racemates), examples:

Examples of the compounds of the formulae (threo-Iba) to (threo-Ibz)(see Table U2) are the compounds of the formulae in question in the formof the racemic mixture of the threo isomers where the meaning of group(R²)_(n) is defined according to a row number of Table 1.

The numeration is carried out according to “(formula) (row number)”without any brackets, for example threo-Iba50=compound of the formula(threo-Iba) with (R²)_(n) according to row 50 of Table 1.

Table 2b (optically active threo-2 enantiomers): Examples:

Examples of the compounds of the formulae (S-Iba) to (threo-2-Ibz) (seeTable U2) are the optically active threo-2 compounds of the formulae inquestion in enriched form [=(3R,4R)-form having more than 90% ee] wherethe meaning of group (R²)_(n) is defined according to a row number ofTable 1.

The numeration is carried out according to “(formula)(row number)”,without any brackets. For example, the No. threo-2-Iba33 refers to thecompound of the formula (S-lba) in which (R²)_(n)=2,4-F₂.

Table 2c (optically active threo-1 enantiomers): Examples:

Examples of the compounds of the formulae (S-lba) to (threo-1-Ibz) (seeTable U2) are the optically active threo-1 compounds of the formulae inquestion in enriched form [=(3S,4S)-form having more than 90% ee] wherethe meaning of group (R²)_(n) is defined according to a row number ofTable 1.

The numeration is carried out according to “(formula) (row number)”,without any brackets. For example, the No. threo-1-Ibb5 refers to thecompound of the formula (S-Ibb) in which (R²)_(n)=4-Me.

Tables 2d, 2e and 2f:

Erythro, erythro-1 and erythro-2 compounds for the compounds of theformulae (Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe), (Ibf), (Ibg), (Ibh),(Ibi), (Ibj), (Ibk), (Ibl), (Ibm), (Ibn), (Ibo), (Ibp), (Ibq), (Ibr),(Ibs), (Ibt), (Ibu), (Ibv), (Ibw), (Ibx), (Iby) and (Ibz), where group(R²)_(n) is as defined in Table 1

For definitions of subformulae of formulae (erythro-Ib), (erythro-1-Ib)and (erythro-2-Ib), see Table U3 below:

TABLE U3 Formula Radical R¹ in formula (erythro-Ib) (erythro-Iba) H(hydrogen atom) (erythro-1-Iba) H (hydrogen atom) (erythro-2-Iba) H(hydrogen atom) (erythro-Ibb) methyl (erythro-1-Ibb) methyl(erythro-2-Ibb) methyl (erythro-Ibc) ethyl (erythro-1-Ibc) ethyl(erythro-2-Ibc) ethyl (erythro-Ibd) n-propyl (erythro-1-Ibd) n-propyl(erythro-2-Ibd) n-propyl (erythro-Ibe) isopropyl (erythro-1-Ibe)isopropyl (erythro-2-Ibe) isopropyl (erythro-Ibf) 2,2-difluoroethyl(erythro-1-Ibf) 2,2-difluoroethyl (erythro-2-Ibf) 2,2-difluoroethyl(erythro-Ibg) 2,2,2-trifluoroethyl (erythro-1-Ibg) 2,2,2-trifluoroethyl(erythro-2-Ibg) 2,2,2-trifluoroethyl (erythro-Ibh) 2-methoxyethyl(erythro-1-Ibh) 2-methoxyethyl (erythro-2-Ibh) 2-methoxyethyl(erythro-Ibi) cyclopropylmethyl (erythro-1-Ibi) cyclopropylmethyl(erythro-2-Ibi) cyclopropylmethyl (erythro-Ibj)(1-methylcyclopropyl)methyl (erythro-1-Ibj) (1-methylcyclopropyl)methyl(erythro-2-Ibj) (1-methylcyclopropyl)methyl (erythro-Ibk) allyl(erythro-1-Ibk) allyl (erythro-2-Ibk) allyl (erythro-Ibl) prop-2-yn-1-yl(erythro-1-Ibl) prop-2-yn-1-yl (erythro-2-Ibl) prop-2-yn-1-yl(erythro-Ibm) ethynyl (erythro-1-Ibm) ethynyl (erythro-2-Ibm) ethynyl(erythro-Ibn) prop-1-yn-1-yl (erythro-1-Ibn) prop-1-yn-1-yl(erythro-2-Ibn) prop-1-yn-1-yl (erythro-Ibo) benzyl (erythro-1-Ibo)benzyl (erythro-2-Ibo) benzyl (erythro-Ibp) 4-chlorobenzyl(erythro-1-Ibp) 4-chlorobenzyl (erythro-2-Ibp) 4-chlorobenzyl(erythro-Ibq) phenyl (erythro-1-Ibq) phenyl (erythro-2-Ibq) phenyl(erythro-Ibr) methoxymethyl (erythro-1-Ibr) methoxymethyl(erythro-2-Ibr) methoxymethyl (erythro-Ibs) difluoromethyl(erythro-1-Ibs) difluoromethyl (erythro-2-Ibs) difluoromethyl(erythro-Ibt) oxetan-3-yl (erythro-1-Ibt) oxetan-3-yl (erythro-2-Ibt)oxetan-3-yl (erythro-Ibu) thietan-3-yl (erythro-1-Ibu) thietan-3-yl(erythro-2-Ibu) thietan-3-yl (erythro-Ibv) 2-(phenylsulphanyl)ethyl(erythro-1-Ibv) 2-(phenylsulphanyl)ethyl (erythro-2-Ibv)2-(phenylsulphanyl)ethyl (erythro-Ibw) 2-(phenylsulphinyl)ethyl(erythro-1-Ibw) 2-(phenylsulphinyl)ethyl (erythro-2-Ibw)2-(phenylsulphinyl)ethyl (erythro-Ibx) 2-(ethylsulphanyl)ethyl(erythro-1-Ibx) 2-(ethylsulphanyl)ethyl (erythro-2-Ibx)2-(ethylsulphanyl)ethyl (erythro-Iby) 2-(ethylsulphinyl)ethyl(erythro-1-Iby) 2-(ethylsulphinyl)ethyl (erythro-2-Iby)2-(ethylsulphinyl)ethyl (erythro-Ibz) tetrahydrofuran-2-ylmethyl(erythro-1-Ibz) tetrahydrofuran-2-ylmethyl (erythro-2-Ibz)tetrahydrofuran-2-ylmethyl

Table 2d (erythro racemates), examples:

Examples of the compounds of the formulae (erythro-Iba) to (erythro-Ibz)(see Table U3) are the compounds of the formulae in question in the formof the racemic mixture of the erythro isomers where the meaning of group(R²)_(n) is defined according to a row number of Table 1.

The numeration is carried out according to “(formula) (row number)”without any brackets, for example erythro-Iba50=compound of the formula(erythro-Iba) with (R²)_(n) according to row 50 of Table 1.

Table 2e (optically active erythro-2 enantiomers): Examples:

Examples of the compounds of the formulae (S-Iba) to (erythro-2-Ibz)(see Table U3) are the optically active erythro-2 compounds of theformulae in question in enriched form [=(3R,4S)-form having more than90% ee] where the meaning of group (R²)_(n) is defined according to arow number of Table 1. The numeration is carried out according to“(formula) (row number)”, without any brackets. For example, the No.erythro-2-Iba33 refers to the compound of the formula (ω-lba) in which(R²)_(n)=2,4-F₂.

Table 2f (optically active erythro-1 enantiomers): Examples:

Examples of the compounds of the formulae (S-Iba) to (erythro-1-Ibz)(see Table U3) are the optically active erythro-1 compounds of theformulae in question in enriched form [=(3S,4R)-form having more than90% ee] where the meaning of group (R²)_(n) is defined according to arow number of Table 1.

The numeration is carried out according to “(formula) (row number)”,without any brackets. For example, the No. erythro-1-Ibb5 refers to thecompound of the formula (S-Ibb) in which (R²)_(n)=4-Me.

Physical data for Tables 2a-2f:

Test methods:

-   1) NMR=1H-NMR data (400 MHz, CDCl₃); characteristic chemical shifts    [in ppm] are indicated for the example in question. The ¹H-NMR    signals were assigned to the erythro and threo diastereomers based    on the C(H)CN doublets. Following EP-A-266725, the doublet at lower    field was assigned to the erythro diastereomer.-   2) MS=mass spectrum, measured using a quadrupole instrument;    electrospray ionization (+−), mass range 100-1000; molecular peak M    or [M+H]+ or [M−1]+ or [M−2]+ or [M+1]+ indicated for the example in    question,-   3) HPLC=High Performance Liquid Chromatography, column: Zorbax    Eclipse, 50×3.0, C18 1.8 ym, mobile phase: water+0.06% formic    acid/acrylonitrile+0.06% formic acid, gradient: 90:10, after 2 min    5:95; detector: DAD (210-400 nm); retention time (rt) indicated for    the example in question,-   4) chiral HPLC═HPLC on a chiral column, column: Chiralpak IC,    250×4.6 mm, 5 μm DAIC 83325, detector wavelength: 210 nm; column    temperature 25° C.,    -   mobile phase a: (n-heptane: 2-propanol), (40:60), Chromasolv,        flow rate: 1.0 ml/min    -   mobile phase b: (n-heptane: 2-propanol), (60:40), Chromasolv,        flow rate: 1.0 ml/min    -   mobile phase c: (n-heptane: 2-propanol), (70:30), Chromasolv,        flow rate: 1.0 ml/min

Ex. Iba1 (diastereomer mixture of erythro-Iba1 and threo-Iba1), NMR,[D₆]-DMSO: 2.60 (dd, 1H, erythro-Iba1), 2.72 (dd, 1H, erythro-Iba1),2.84 (m, 2H, threo-Iba1), 3.61 (m, 1H, erythro-Iba1), 3.72 (m, 1H,threo-Iba1), 4.68 (d, 1H, threo-Iba1), 4.75 (d, 1H, erythro-Iba1)

Ex. Iba2 (diastereomer mixture of erythro-Iba2 and threo-Iba2), NMR:2.88 (m, 1H, threo-Iba2), 3.11 (dd, 1H, erythro-Iba2), 3.53 (m, 1H,erythro-Iba2), 3.71 (q, 1H, threo-Iba2), 4.23 (d, 1H, threo-Iba2), 4.61(d, 1H, erythro-Iba2)

Ex. erythro-Ibb1, NMR: 2.87 (dd, 1H), 3.05 (dd, 1H), 3.53 (q, 1H), 3.69(s, 3H), 4.47 (d, 1H), 6.96 (m, 4H), 7.21 (m, 1H), 7.30 (d, 1H), 8.40(bs, 1H), 8.56 (m, 1H)

Ex. threo-Ibb1, NMR: 2.90 (m, 2H), 3.59 (s, 3H), 3.67 (q, 1H), 4.12 (d,1H), 6.98 (t, 2H), 7.06 (m, 2H), 7.27 (m, 1H), 7.48 (d, 1H), 8.32 (bs,1H), 8.57 (bs, 1H)

Ex. erythro-Ibb2, NMR: 2.85 (dd, 1H), 3.02 (dd, 1H), 3.53 (m, 1H), 3.69(s, 3H), 4.48 (d, 1H), 6.96 (d, 2H), 7.24 (m, 1H), 7.25 (d, 2H), 7.32(m, 1H), 8.40 (m, 1H), 8.56 (m, 1H)

Ex. erythro-1-Ibb2, chiral HPLC: 6.3 min, mobile phase a

Ex. erythro-2-Ibb2, chiral HPLC: 8.6 min, mobile phase a

Ex. threo-Ibb2, NMR: 2.89 (m, 2H), 3.58 (s, 3H), 3.66 (q, 1H), 4.12 (m,1H), 7.02 (d, 2H), 7.25 (d, 2H), 7.27 (m, 1H), 7.49 (m, 1H), 8.35 (m,1H), 8.57 (m, 1H)

Ex. threo-1-Ibb2, NMR: 2.89 (m, 2H), 3.58 (s, 3H), 3.66 (q, 1H), 4.12(d, 1H), 7.02 (d, 2H), 7.25 (d, 2H), 7.27 (m, 1H), 7.49 (m, 1H), 8.35(m, 1H), 8.57 (m, 1H); chiral HPLC: 13.1 min, mobile phase a

Ex. threo-2-Ibb2, NMR: 2.89 (m, 2H), 3.58 (s, 3H), 3.66 (q, 1H), 4.12(d, 1H), 7.02 (d, 2H), 7.25 (d, 2H), 7.27 (m, 1H), 7.49 (m, 1H), 8.35(m, 1H), 8.57 (m, 1H); chiral HPLC: 14.9 min, mobile phase a

Ex. erythro-Ibc2, NMR: 1.23 (t, 3H), 2.82 (dd, 1H), 3.01 (dd, 1H), 3.51(m, 1H), 4.12 (q, 2H), 4.46 (d, 1H), 6.92 (d, 2H), 7.21 (m, 1H), 7.22(d, 2H), 7.33 (m, 1H), 8.41 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibc2, NMR: 1.14 (t, 3H), 2.89 (m, 2H), 3.64 (q, 1H), 4.03 (m,2H), 4.12 (d, 1H), 7.02 (d, 2H), 7.26 (d, 2H), 7.27 (m, 1H), 7.48 (m,1H), 8.35 (m, 1H), 8.58 (m, 1H)

Ex. erythro-Ibd2, NMR: 0.88 (t, 3H), 1.60 (quint, 2H), 2.86 (dd, 1H),3.03 (dd, 1H), 3.52 (q, 1H), 4.02 (t, 2H), 4.47 (d, 1H), 6.93 (d, 2H),7.24 (m, 1H), 7.25 (d, 2H), 7.31 (m, 1H), 8.41 (m, 1H), 8.57 (m, 1H)

Ex. threo-Ibd2, NMR: 0.83 (t, 3H), 1.54 (quint, 2H), 2.88 (m, 2H), 3.64(q, 1H), 3.91 (t, 2H), 4.12 (d, 1H), 7.02 (d, 2H), 7.25 (d, 2H), 7.27(m, 1H), 7.48 (m, 1H), 8.34 (m, 1H), 8.56 (m, 1H)

Ex. erythro-Ibe2, 1.18 (d, 3H), 1.21 (d, 3H), 2.80 (dd, 1H), 2.98 (dd,1H), 3.51 (m, 1H), 4.45 (d, 1H), 4.97 (sept, 1H), 6.93 (d, 2H), 7.24 (m,1H), 7.25 (d, 2H), 7.31 (m, 1H), 8.41 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibe2, NMR: 1.09 (d, 3H), 1.12 (d, 3H), 2.85 (m, 2H), 3.63 (m,1H), 4.11 (d, 1H), 4.87 (sept, 1H), 7.02 (d, 2H), 7.25 (d, 2H), 7.27 (m,1H), 7.47 (m, 1H), 8.34 (m, 1H), 8.58 (m, 1H)

Ex. Iba3 (diastereomer mixture of erythro-Iba3 and threo-Iba3), NMR,[D₆]-DMSO: 2.57 (dd, 1H, erythro-Iba3), 2.70 (dd, 1H, erythro-Iba3),2.84 (d, 2H, threo-Iba3), 3.61 (m, 1H, erythro-Iba3), 3.71 (m, 1H,threo-Iba3), 4.70 (d, 1H, threo-Iba3), 4.77 (d, 1H, erythro-Iba3)

Ex. erythro-Ibb3, NMR: 2.85 (dd, 1H), 3.04 (dd, 1H), 3.52 (m, 1H), 3.69(s, 3H), 4.48 (d, 1H), 6.88 (d, 2H), 7.23 (m, 1H), 7.33 (m, 1H), 7.39(d, 2H), 8.41 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibb3, NMR: 2.89 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.15 (d,1H), 6.98 (d, 2H), 7.29 (m, 1H), 7.42 (d, 2H), 7.49 (m, 1H), 8.36 (m,1H), 8.58 (m, 1H)

Ex. threo-1-Ibb3, NMR: 2.89 (m, 2H), 3.60 (s, 3H), 3.65 (q, 1H), 4.15(d, 1H), 6.98 (d, 2H), 7.29 (m, 1H), 7.42 (d, 2H), 7.49 (m, 1H), 8.36(m, 1H), 8.58 (m, 1H); chiral HPLC: 10.5 min, Eluent b

Ex. threo-2-Ibb3, NMR: 2.89 (m, 2H), 3.60 (s, 3H), 3.66 (q, 1H), 4.15(d, 1H), 6.98 (d, 2H), 7.29 (m, 1H), 7.42 (d, 2H), 7.49 (m, 1H), 8.36(m, 1H), 8.58 (m, 1H); chiral HPLC: 21.9 min, Eluent b

Ex. erythro-Ibc3, NMR: 1.22 (t, 3H), 2.82 (dd, 1H), 3.01 (dd, 1H), 3.51(m, 1H), 4.12 (q, 2H), 4.47 (d, 1H), 6.88 (d, 2H), 7.22 (m, 1H), 7.33(m, 1H), 7.38 (d, 2H), 8.40 (m, 1H), 8.56 (m, 1H)

Ex. threo-Ibc3, NMR: 1.12 (t, 3H), 2.88 (m, 2H), 3.63 (q, 1H), 4.02 (m,2H), 4.12 (d, 1H), 6.97 (d, 2H), 7.28 (m, 1H), 7.40 (d, 2H), 7.48 (m,1H), 8.33 (m, 1H), 8.58 (m, 1H)

Ex. erythro-Ibb4, NMR: 2.85 (dd, 1H), 3.03 (dd, 1H), 3.50 (m, 1H), 3.70(s, 3H), 4.48 (d, 1H), 6.78 (d, 2H), 7.23 (m, 1H), 7.34 (m, 1H), 7.49(d, 2H), 8.41 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibb4, NMR: 2.89 (m, 2H), 3.59 (s, 3H), 3.63 (q, 1H), 4.14 (d,1H), 6.85 (d, 2H), 7.29 (m, 1H), 7.49 (m, 1H), 7.63 (d, 2H), 8.38 (m,1H), 8.58 (m, 1H)

Ex. Iba5 (diastereomer mixture of erythro-Iba5 and threo-Iba5), NMR,[D₆]-DMSO: 2.21 (s, 3H, threo-Iba5), 2.25 (s, 3H, erythro-Iba5), 3.50(m, 1H, erythro-Iba5), 3.62 (m, 1H, threo-Iba5), 4.65 (d, 1H,threo-Iba5), 4.71 (d, 1H, erythro-Iba5)

Ex. erythro-Ibb5, NMR: 2.29 (s, 3H), 2.85 (dd, 1H), 3.02 (dd, 1H), 3.51(m, 1H), 3.68 (s, 3H), 4.44 (d, 1H), 6.88 (d, 2H), 7.05 (d, 2H), 7.19(m, 1H), 7.32 (m, 1H), 8.37 (m, 1H), 8.53 (m, 1H)

Ex. erythro-1-Ibb5, chiral HPLC: 6.3 min, Eluent a

Ex. erythro-2-Ibb5, chiral HPLC: 8.7 min, Eluent a

Ex. threo-Ibb5, NMR: 2.29 (s, 3H), 2.91 (d, 2H), 3.59 (s, 3H), 3.62 (q,1H), 4.13 (d, 1H), 6.95 (d, 2H), 7.08 (d, 2H), 7.25 (m, 1H), 7.50 (m,1H), 8.30 (m, 1H), 8.53 (m, 1H);

Ex. threo-1-Ibb5, NMR: 2.29 (s, 3H), 2.91 (d, 2H), 3.59 (s, 3H), 3.62(q, 1H), 4.13 (d, 1H), 6.95 (d, 2H), 7.08 (d, 2H), 7.25 (m, 1H), 7.50(m, 1H), 8.30 (m, 1H), 8.53 (m, 1H); chiral HPLC: 13.1 min, Eluent a

Ex. threo-2-Ibb5, NMR: 2.29 (s, 3H), 2.91 (d, 2H), 3.59 (s, 3H), 3.62(q, 1H), 4.13 (d, 1H), 6.95 (d, 2H), 7.08 (d, 2H), 7.25 (m, 1H), 7.50(m, 1H), 8.30 (m, 1H), 8.53 (m, 1H); chiral HPLC: 14.9 min, Eluent a

Ex. erythro-IbcS, NMR: 1.22 (t, 3H), 2.29 (s, 3H), 2.83 (dd, 1H), 3.01(dd, 1H), 3.50 (m, 1H), 4.11 (q, 2H), 4.43 (d, 1H), 6.89 (d, 2H), 7.05(d, 2H), 7.20 (m, 1H), 7.32 (m, 1H), 8.38 (m, 1H), 8.53 (m, 1H)

Ex. threo-IbcS, NMR: 1.12 (t, 3H), 2.29 (s, 3H), 2.89 (m, 2H), 3.62 (q,1H), 4.01 (m, 2H), 4.12 (d, 1H), 6.95 (d, 2H), 7.08 (d, 2H), 7.25 (m,1H), 7.49 (m, 1H), 8.30 (m, 1H), 8.55 (m, 1H)

Ex. erythro-Ibv5, NMR: 2.29 (s, 3H), 2.80 (dd, 1H), 2.98 (dd, 1H), 3.06(t, 2H), 3.47 (m, 1H), 4.22 (t, 2H), 4.42 (d, 1H), 6.87 (d, 2H), 7.05(d, 2H), 8.36 (m, 1H), 8.54 (m, 1H)

Ex. threo-Ibv5, NMR: 2.29 (s, 3H), 2.87 (m, 2H), 2.96 (t, 2H), 3.58 (q,1H), 4.11 (d, 1H), 4.12 (t, 2H), 6.93 (d, 2H), 7.07 (d, 2H), 7.49 (m,1H), 8.30 (m, 1H), 8.54 (m, 1H)

Ex. Iba7 (diastereomer mixture of erythro-Iba7 and threo-Iba7), NMR:3.70 (m, 1H, erythro-Iba7), 3.85 (q, 1H, threo-Iba7), 4.29 (d, 1H,threo-Iba7), 4.67 (d, 1H, erythro-Iba7)

Ex. erythro-Ibb7, NMR: 2.91 (dd, 1H), 3.09 (dd, 1H), 3.69 (m, 1H), 3.70(s, 3H), 4.54 (d, 1H), 7.24 (d, 2H), 7.26 (m, 1H), 7.36 (m, 1H), 8.13(d, 2H), 8.44 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb7, NMR: 2.97 (m, 2H), 3.60 (s, 3H), 3.81 (q, 1H), 4.20 (d,1H), 7.30 (d, 2H), 7.29 (m, 1H), 7.50 (m, 1H), 8.17 (d, 2H), 8.37 (m,1H), 8.59 (m, 1H)

Ex. erythro-Ibb8, NMR: 2.83 (dd, 1H), 3.02 (dd, 1H), 3.48 (m, 1H), 3.67(s, 3H), 3.77 (s, 3H), 4.43 (d, 1H), 6.77 (d, 2H), 6.91 (d, 2H), 7.19(m, 1H), 7.30 (m, 1H), 8.38 (m, 1H), 8.53 (m, 1H)

Ex. threo-Ibb8, NMR: 2.88 (m, 2H), 3.57 (s, 3H), 3.62 (q, 1H), 3.76 (s,3H), 4.11 (m, 1H), 6.78 (d, 2H), 6.97 (d, 2H), 7.22 (m, 1H), 7.47 (m,1H), 8.31 (m, 1H), 8.54 (m, 1H)

Ex. Ibc8 (diastereomer mixture of erythro-Ibc8 and threo-Ibc8), NMR:1.15 (t, 3H, threo-Ibc8), 1.21 (t, 3H, erythro-Ibc8), 2.83 (dd, 1H,erythro-Ibc8), 2.88 (m, 2H, threo-Ibc8), 3.02 (dd, 1H, erythro-Ibc8),3.49 (m, 1H, erythro-Ibc8), 3.62 (m, 1H, threo-Ibc8), 3.68 (s, 3H,erythro-Ibc8+3H, threo-Ibc8), 4.03 (m, 2H, threo-Ibc8), 4.12 (m, 2H,erythro-Ibc8+1H threo-Ibc8), 4.43 (d, 1H, erythro-Ibc8)

Ex. erythro-Ibc8, NMR: 1.21 (t, 3H), 2.83 (dd, 1H), 3.02 (dd, 1H), 3.49(m, 1H), 3.68 (s, 3H), 4.12 (q, 2H), 4.43 (d, 1H), 6.78 (d, 2H), 6.92(d, 2H), 7.20 (m, 1H), 7.31 (m, 1H), 8.38 (m, 1H), 8.54 (m, 1H)

Ex. Iba9 (diastereomer mixture of erythro-Iba9 and threo-Iba9), NMR,[D₆]-DMSO: 1.10 (d, 6H, threo-Iba9), 1.18 (d, 6H, erythro-Iba9), 4.61(d, 1H, threo-Iba9), 4.68 (d, 1H, erythro-Iba9), 8.30 (m, 1H,threo-Iba9), 8.40 (m, 1H, erythro-Iba9), 8.46 (m, 1H, threo-Iba9), 8.52(m, 1H, erythro-Iba9)

Ex. erythro-Ibb9, NMR: 1.20 (m, 6H), 2.83 (m, 2H), 3.03 (dd, 1H), 3.51(m, 1H), 3.68 (s, 3H), 4.46 (d, 1H), 6.91 (d, 2H), 7.10 (d, 2H), 7.18(m, 1H), 7.30 (m, 1H), 8.37 (m, 1H), 8.53 (m, 1H)

Ex. threo-Ibb9, NMR: 1.20 (d, 6H), 2.88 (m, 3H), 3.55 (s, 3H), 3.63 (q,1H), 4.15 (d, 1H), 7.00 (d, 2H), 7.12 (d, 2H), 7.24 (m, 1H), 7.48 (m,1H), 8.35 (m, 1H), 8.54 (m, 1H)

Ex. erythro-Ibc9, NMR: 1.20 (m, 9H), 2.84 (m, 2H), 3.03 (dd, 1H), 3.52(m, 1H), 4.12 (q, 2H), 4.46 (d, 1H), 6.92 (d, 2H), 7.10 (d, 2H), 7.19(m, 1H), 7.31 (m, 1H), 8.39 (m, 1H), 8.54 (m, 1H)

Ex. threo-Ibc9, NMR: 1.10 (t, 3H), 1.20 (d, 6H), 2.88 (m, 3H), 3.62 (q,1H), 4.01 (q, 2H), 4.17 (d, 1H), 7.00 (d, 2H), 7.12 (d, 2H), 7.25 (m,1H), 7.49 (m, 1H), 8.36 (m, 1H), 8.55 (m, 1H)

Ex. erythro-Ibb10, NMR: 2.89 (dd, 1H), 3.09 (dd, 1H), 3.51 (m, 1H), 3.70(s, 3H), 3.90 (s, 3H), 4.50 (d, 1H), 7.10 (d, 2H), 7.20 (m, 1H), 7.30(m, 1H), 7.92 (d, 2H), 8.42 (m, 1H), 8.56 (m, 1H)

Ex. threo-Ibb10, NMR: 2.96 (m, 2H), 3.59 (s, 3H), 3.75 (m, 1H), 3.92 (s,3H), 4.17 (d, 1H), 7.18 (d, 2H), 7.25 (m, 1H), 7.48 (m, 1H), 7.95 (d,2H), 8.35 (m, 1H), 8.56 (m, 1H)

Ex. Iba11 (diastereomer mixture of erythro-Iba11 and threo-Iba11), NMR,[D₆]-DMSO: 3.69 (m, 1H, erythro-Iba11), 3.79 (q, 1H, threo-Iba11), 4.75(d, 1H, threo-Iba11), 4.81 (d, 1H, erythro-Iba11), 7.30 (d, 2H,threo-Iba11), 7.39 (d, 2H, erythro-Iba11), 7.80 (d, 2H, threo-Iba11),7.89 (d, 2H, erythro-Iba11)

Ex. Iba12 (diastereomer mixture of erythro-Iba12 and threo-Iba12), NMR,[D₆]-DMSO: 2.59 (dd, 1H, erythro-Iba12), 2.79 (dd, 1H, erythro-Iba12),2.90 (m, 2H, threo-Iba12), 3.75 (m, 1H, erythro-Iba12), 3.85 (m, 1H,threo-Iba12), 4.78 (d, 1H, threo-Iba12), 4.81 (d, 1H, erythro-Iba12)

Ex. erythro-Ibb12, NMR: 2.88 (dd, 1H), 3.09 (dd, 1H), 3.65 (m, 1H), 3.70(s, 3H), 4.51 (d, 1H), 7.15 (d, 2H), 7.22 (m, 1H), 7.32 (m, 1H), 7.53(d, 2H), 8.43 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb12, NMR: 2.95 (d, 2H), 3.59 (s, 3H), 3.76 (q, 1H), 4.20 (d,1H), 7.26 (d, 2H), 7.29 (m, 1H), 7.50 (m, 1H), 7.58 (d, 2H), 8.39 (m,1H), 8.58 (m, 1H)

Ex. Iba13 (diastereomer mixture of erythro-Iba13 and threo-Iba13), NMR,[D₆]-DMSO: 3.69 (m, 1H, erythro-Iba13), 3.79 (q, 1H, threo-Iba13), 4.72(d, 1H, threo-Iba13), 4.78 (d, 1H, erythro-Iba13), 8.35 (m, 1H,threo-Iba13), 8.48 (m, 1H, threo-Iba13), 8.50 (m, 1H, erythro-Iba13),8.58 (m, 1H, erythro-Iba13)

Ex. erythro-Ibb13, NMR: 2.87 (dd, 1H), 3.08 (dd, 1H), 3.58 (m, 1H), 3.70(s, 3H), 4.49 (d, 1H), 7.05 (d, 2H), 7.11 (d, 2H), 7.21 (m, 1H), 7.30(m, 1H), 8.43 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibb13, NMR: 2.90 (d, 2H), 3.60 (s, 3H), 3.70 (q, 1H), 4.16 (d,1H), 7.17 (s, 4H), 7.29 (m, 1H), 7.48 (m, 1H), 8.38 (m, 1H), 8.59 (m,1H)

Ex. Iba14 (diastereomer mixture of erythro-Iba14 and threo-Iba14), NMR,[D₆]-DMSO: 2.70 (dd, 1H, erythro-Iba14), 2.85 (d, 2H, threo-Iba14), 3.65(m, 1H, erythro-Iba14), 3.75 (q, 1H, threo-Iba14), 4.70 (d, 1H,threo-Iba14), 4.77 (d, 1H, erythro-Iba14)

Ex. erythro-Ibb14, NMR: 2.85 (dd, 1H), 3.02 (dd, 1H), 3.56 (m, 1H), 3.70(s, 3H), 4.48 (d, 1H), 6.75 (m, 1H), 6.80 (m, 1H), 6.97 (m, 1H), 7.21(m, 2H), 7.35 (m, 1H), 8.41 (m, 1H), 8.57 (m, 1H)

Ex. threo-Ibb14, NMR: 2.92 (m, 2H), 3.59 (s, 3H), 3.67 (q, 1H), 4.16 (d,1H), 6.80 (m, 1H), 6.89 (m, 1H), 6.97 (m, 1H), 7.27 (m, 2H), 7.50 (m,1H), 8.36 (m, 1H), 8.57 (m, 1H)

Ex. erythro-Ibb15, NMR: 2.84 (dd, 1H), 3.01 (dd, 1H), 3.52 (m, 1H), 3.68(s, 3H), 4.47 (d, 1H), 6.91 (m, 1H), 6.98 (m, 1H), 7.22 (m, 2H), 7.25(m, 1H), 7.33 (m, 1H), 8.41 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibb15, NMR: 2.90 (m, 2H), 3.58 (s, 3H), 3.64 (q, 1H), 4.13 (d,1H), 6.99 (m, 1H), 7.08 (m, 1H), 7.23 (m, 2H), 7.28 (m, 1H), 7.50 (m,1H), 8.36 (m, 1H), 8.58 (m, 1H)

Ex. erythro-Ibb17, NMR: 2.27 (s, 3H), 2.85 (dd, 1H), 3.03 (dd, 1H), 3.51(m, 1H), 3.69 (s, 3H), 4.45 (d, 1H), 6.81 (m, 2H), 7.08 (d, 1H), 7.14(t, 1H), 7.20 (m, 1H), 7.32 (m, 1H), 8.38 (m, 1H), 8.54 (m, 1H)

Ex. threo-Ibb17, NMR: 2.29 (s, 3H), 2.92 (d, 2H), 3.58 (s, 3H), 3.62 (q,1H), 4.15 (d, 1H), 6.88 (m, 2H), 7.06 (d, 1H), 7.17 (t, 1H), 7.26 (m,1H), 7.49 (m, 1H), 8.33 (m, 1H), 8.54 (m, 1H)

Ex. Iba18 (diastereomer mixture of erythro-Iba18 and threo-Iba18), NMR:3.62 (m, 1H, erythro-Iba18), 3.69 (q, 1H, threo-Iba18), 4.30 (d, 1H,threo-Iba18), 4.69 (d, 1H, erythro-Iba18)

Ex. erythro-Ibb18, NMR: 2.88 (dd, 1H), 3.05 (dd, 1H), 3.60 (m, 1H), 3.70(s, 3H), 4.50 (d, 1H), 7.25 (m, 2H), 7.33 (m, 2H), 7.42 (t, 1H), 7.60(m, 1H), 8.42 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb18, NMR: 2.95 (m, 2H), 3.60 (s, 3H), 3.71 (m, 1H), 4.18 (d,1H), 7.30 (m, 1H), 7.40 (m, 3H), 7.50 (m, 1H), 7.59 (m, 1H), 8.36 (m,1H), 8.59 (m, 1H)

Ex. Iba19 (diastereomer mixture of erythro-Iba19 and threo-Iba19), NMR:3.74 (m, 1H, erythro-Iba19), 3.89 (q, 1H, threo-Iba19), 4.38 (d, 1H,threo-Iba19), 4.70 (d, 1H, erythro-Iba19)

Ex. erythro-Ibc19, NMR: 1.22 (t, 3H), 2.89 (dd, 1H), 3.03 (dd, 1H), 3.70(q, 1H), 4.13 (q, 2H), 4.51 (d, 1H), 7.26 (m, 1H), 7.40 (m, 1H), 7.48(m, 2H), 7.88 (m, 1H), 8.18 (m, 1H), 8.45 (m, 1H), 8.60 (m, 1H)

Ex. threo-Ibc19, NMR: 1.17 (t, 3H), 2.98 (m, 2H), 3.81 (q, 1H), 4.05 (m,2H), 4.22 (d, 1H), 7.30 (m, 1H), 7.50 (m, 3H), 7.98 (m, 1H), 8.15 (m,1H), 8.37 (m, 1H), 8.59 (m, 1H)

Ex. erythro-Ibb21, NMR: 2.89 (dd, 1H), 3.10 (dd, 1H), 3.62 (m, 1H), 3.69(s, 3H), 4.51 (d, 1H), 7.12 (s, 1H), 7.20 (m, 1H), 7.29 (m, 2H), 7.42(t, 1H), 7.55 (d, 1H), 8.41 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibb21, NMR: 2.94 (m, 2H), 3.59 (s, 3H), 3.76 (q, 1H), 4.18 (d,1H), 7.28 (m, 2H), 7.32 (m, 1H), 7.45 (m, 2H), 7.55 (d, 1H), 8.34 (m,1H), 8.57 (m, 1H)

Ex. Iba23 (diastereomer mixture of erythro-Iba23 and threo-Iba23), NMR:2.88 (dd, 1H, erythro-Iba23), 3.05 (m, 2H, threo-Iba23), 3.10 (dd, 1H,erythro-Iba23), 4.00 (m, 1H, erythro-Iba23+1H, threo-Iba23), 4.29 (d,1H, threo-Iba23), 4.60 (d, 1H, erythro-Iba23)

Ex. Ibb23 (diastereomer mixture of erythro-Ibb23 and threo-Ibb23), NMR:2.82 (dd, 1H, erythro-Ibb23), 3.00 (dd, 1H, erythro-Ibb23), 3.02 (m, 2H,threo-Ibb23), 3.58 (s, 3H, threo-Ibb23), 3.68 (s, 3H, erythro-Ibb23),3.98 (m, 1H, erythro-Ibb23+1H, threo-Ibb23), 4.22 (d, 1H, threo-Ibb23),4.50 (d, 1H, erythro-Ibb23)

Ex. erythro-Ibb32, NMR: 2.82 (dd, 1H), 3.00 (dd, 1H), 3.68 (s, 3H), 4.00(q, 1H), 4.52 (d, 1H), 7.13 (m, 3H), 7.27 (m, 1H), 7.47 (m, 1H), 8.44(m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb32, NMR: 3.01 (m, 2H), 3.59 (s, 3H), 4.00 (m, 1H), 4.21 (d,1H), 6.90 (m, 1H), 7.05 (m, 2H), 7.31 (m, 1H), 7.68 (m, 1H), 8.43 (m,1H), 8.58 (m, 1H)

Ex. erythro-Ibb33, NMR: 2.80 (dd, 1H), 2.99 (dd, 1H), 3.68 (s, 3H), 3.4(m, 1H), 4.49 (d, 1H), 6.69 (m, 1H), 6.92 (m, 1H), 7.25 (m, 1H), 7.39(m, 1H), 7.45 (m, 1H), 8.45 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb33, NMR, [D₆]-DMSO: 2.98 (m, 2H), 3.48 (s, 3H), 4.00 (m,1H), 4.68 (d, 1H), 7.05 (m, 2H), 7.38 (m, 1H), 7.43 (m, 1H), 7.69 (m,1H), 8.28 (m, 1H), 8.47 (m, 1H)

Ex. erythro-Ibb34, NMR: 2.79 (dd, 1H), 2.96 (dd, 1H), 3.68 (s, 3H), 3.98(q, 1H), 4.50 (d, 1H), 6.89 (m, 1H), 6.97 (m, 1H), 7.10 (m, 1H), 7.25(m, 1H), 7.49 (m, 1H), 8.45 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb34, NMR: 2.98 (m, 2H), 3.59 (s, 3H), 3.92 (q, 1H), 4.22 (d,1H), 6.85 (m, 1H), 6.95 (m, 1H), 6.99 (m, 1H), 7.30 (m, 1H), 7.68 (m,1H), 8.45 (m, 1H), 8.59 (m, 1H)

Ex. erythro-Ibb35, NMR: 2.80 (dd, 1H), 2.86 (dd, 1H), 3.55 (s, 3H), 4.12(q, 1H), 4.37 (d, 1H), 6.92 (t, 2H), 7.29 (m, 1H), 7.35 (m, 1H), 7.73(m, 1H), 8.57 (m, 1H), 8.64 (m, 1H)

Ex. threo-Ibb35, NMR: 3.14 (dd, 1H), 3.26 (dd, 1H), 3.62 (s, 3H), 4.18(m, 1H), 4.21 (d, 1H), 6.75 (t, 2H), 7.14 (m, 1H), 7.25 (m, 1H), 7.67(m, 1H), 8.26 (m, 1H), 8.48 (m, 1H)

Ex. threo-2-Ibb35, NMR: 3.14 (dd, 1H), 3.26 (dd, 1H), 3.62 (s, 3H), 4.18(m, 1H), 4.22 (d, 1H), 6.75 (t, 2H), 7.14 (m, 1H), 7.25 (m, 1H), 7.67(m, 1H), 8.27 (m, 1H), 8.49 (m, 1H); chiral HPLC: 21.8 min, Eluent c

Ex. erythro-Ibb36, NMR: 2.84 (dd, 1H), 3.01 (dd, 1H), 3.52 (q, 1H), 3.69(s, 3H), 4.46 (d, 1H), 6.74 (m, 1H), 6.87 (m, 1H), 7.04 (m, 1H), 7.25(m, 1H), 7.35 (m, 1H), 8.43 (bs, 1H), 8.58 (bs, 1H)

Ex. threo-Ibb36, NMR: 2.89 (m, 2H), 3.60 (s, 3H), 3.63 (q, 1H), 4.13 (d,1H), 6.84 (m, 1H), 6.93 (m, 1H), 7.08 (m, 1H), 7.29 (m, 1H), 7.51 (m,1H), 8.36 (bs, 1H), 8.58 (m, 1H)

Ex. erythro-Ibb37, NMR: 2.82 (dd, 1H), 3.00 (dd, 1H), 3.53 (q, 1H), 3.70(s, 3H), 4.57 (d, 1H), 6.59 (m, 2H), 6.73 (m, 1H), 7.25 (m, 1H), 7.40(m, 1H), 8.45 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibb37, NMR: 2.90 (m, 2H), 3.61 (s, 3H), 3.65 (q, 1H), 4.14 (m,1H), 6.66 (m, 2H), 6.72 (m, 1H), 7.30 (m, 1H), 7.54 (m, 1H), 8.39 (m,1H), 8.59 (m, 1H)

Ex. threo-1-Ibb37, chiral HPLC: 9.8 min, Eluent c

Ex. threo-2-Ibb37, NMR: 2.90 (m, 2H), 3.61 (s, 3H), 3.65 (q, 1H), 4.14(m, 1H), 6.66 (m, 2H), 6.72 (m, 1H), 7.30 (m, 1H), 7.54 (m, 1H), 8.39(m, 1H), 8.59 (m, 1H); chiral HPLC: 15.8 min, Eluent c

Ex. erythro-Ibb38, NMR: 2.79 (m, 1H), 2.96 (m, 1H), 3.48 (m, 1H), 3.69(s, 3H), 4.43 (m, 1H), 6.59 (m, 1H), 6.69 (m, 1H), 7.28 (m, 1H), 7.40(m, 1H), 8.45 (m, 1H), 8.60 (m, 1H)

Ex. threo-Ibb38, NMR: 2.88 (m, 2H), 3.60 (m, 1H), 3.61 (s, 3H), 4.12 (m,1H), 6.69 (m, 1H), 6.78 (m, 1H), 7.31 (m, 1H), 7.53 (m, 1H), 8.39 (m,1H), 8.60 (m, 1H)

Ex. erythro-Ibc43, NMR: 1.25 (t, 3H), 2.81 (dd, 1H), 3.00 (dd, 1H), 3.52(m, 1H), 4.12 (q, 2H), 4.46 (d, 1H), 6.89 (dd, 1H), 7.10 (d, 1H), 7.25(m, 1H), 7.34 (d, 2H), 7.38 (m, 1H), 8.45 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibc43, NMR: 1.18 (t, 3H), 2.90 (m, 2H), 3.65 (m, 1H), 4.04 (m,2H), 4.15 (d, 1H), 6.96 (dd, 1H), 7.19 (d, 1H), 7.30 (m, 1H), 7.37 (d,2H), 7.51 (m, 1H), 8.39 (m, 1H), 8.59 (m, 1H)

Ex. erythro-Ibb49, NMR: 2.84 (m, 2H), 3.58 (s, 3H), 4.05 (q, 1H), 4.38(d, 1H), 6.97 (d, 2H), 7.42 (m, 1H), 7.79 (m, 1H), 8.60 (s, 1H), 8.67(d, 1H)

Ex. threo-Ibb49, NMR: 3.10 (dd, 1H), 3.24 (dd, 1H), 3.65 (s, 3H), 4.15(m, 1H), 4.05 (d, 1H), 6.81 (d, 2H), 7.35 (m, 1H), 7.73 (m, 1H), 8.32(s, 1H), 8.54 (d, 1H)

Ex. erythro-Ibb50, NMR: 2.85 (dd, 1H), 3.01 (dd, 1H), 3.54 (q, 1H), 3.70(s, 3H), 4.48 (d, 1H), 6.75 (dd, 1H), 6.85 (dd, 1H), 7.25 (m, 1H), 7.30(d, 1H), 7.38 (m, 1H), 8.44 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb50, NMR: 2.90 (m, 2H), 3.60 (s, 3H), 3.67 (q, 1H), 4.13 (d,1H), 6.86 (dd, 1H), 6.90 (dd, 1H), 7.30 (m, 1H), 7.32 (d, 1H), 7.52 (m,1H), 8.39 (m, 1H), 8.59 (m, 1H)

Ex. erythro-Ibb51, NMR: 2.83 (dd, 1H), 3.01 (dd, 1H), 3.52 (q, 1H), 3.68(s, 3H), 4.47 (d, 1H), 6.68 (dd, 1H), 6.81 (dd, 1H), 7.25 (m, 1H), 7.38(d, 1H), 7.44 (dd, 1H), 8.43 (m, 1H), 8.58 (m, 1H)

Ex. threo-Ibb51, NMR: 2.89 (m, 2H), 3.60 (s, 3H), 3.63 (q, 1H), 4.13 (d,1H), 6.80 (dd, 1H), 6.89 (dd, 1H), 7.30 (m, 1H), 7.48 (dd, 1H), 7.51 (m,1H), 8.38 (m, 1H), 8.59 (m, 1H)

Ex. erythro-Ibb55, NMR: 2.82 (dd, 1H), 3.01 (dd, 1H), 3.52 (m, 1H), 3.70(s, 3H), 4.48 (d, 1H), 6.90 (m, 1H), 7.05 (t, 1H), 7.07 (m, 1H), 7.25(m, 1H), 7.35 (m, 1H), 8.44 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb55, NMR: 2.88 (m, 2H), 3.60 (s, 3H), 3.65 (m, 1H), 4.13 (m,1H), 6.99 (m, 1H), 7.08 (t, 1H), 7.13 (m, 1H), 7.30 (m, 1H), 7.50 (m,1H), 8.38 (m, 1H), 8.59 (m, 1H)

Ex. erythro-Ibb56, NMR: 2.81 (dd, 1H), 2.99 (dd, 1H), 3.52 (q, 1H), 3.70(s, 3H), 4.48 (d, 1H), 6.70 (m, 1H), 6.81 (m, 1H), 7.02 (m, 1H), 7.27(m, 1H), 7.38 (m, 1H), 8.46 (m, 1H), 8.59 (m, 1H)

Ex. threo-Ibb56, NMR: 2.89 (m, 2H), 3.60 (s, 3H), 3.63 (q, 1H), 4.12 (m,1H), 6.75 (m, 1H), 6.91 (m, 1H), 7.01 (m, 1H), 7.30 (m, 1H), 7.53 (m,1H), 8.38 (m, 1H), 8.59 (m, 1H)

Ex. erythro-Ibb75, NMR: 2.87 (dd, 1H), 3.05 (dd, 1H), 3.62 (q, 1H), 3.70(s, 1H), 4.60 (d, 1H), 7.17 (t, 1H), 7.30 (m, 2H), 7.42 (m, 1H), 7.53(m, 1H), 8.55 (s, 1H), 8.65 (d, 1H)

Ex. threo-Ibb75, NMR: 2.91 (m, 2H), 3.61 (s, 1H), 3.75 (q, 1H), 4.33 (d,1H), 7.20 (t, 1H), 7.42 (m, 2H), 7.58 (m, 1H), 7.80 (m, 1H), 8.56 (s,1H), 8.69 (d, 1H)

(B) FORMULATION EXAMPLES

-   a) A dusting product is obtained by mixing 10 parts by weight of a    compound of the formula (I) and 90 parts by weight of talc as inert    substance and comminuting the mixture in a hammer mill.-   b) A wettable powder which is readily dispersible in water is    obtained by mixing 25 parts by weight of a compound of the formula    (I), 64 parts by weight of kaolin-containing quartz as inert    substance, 10 parts by weight of potassium lignosulphonate and 1    part by weight of sodium oleoylmethyltaurate as wetting agent and    dispersant, and grinding the mixture in a pinned-disc mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) with 6    parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3    parts by weight of isotridecanol polyglycol ether (8 EO) and 71    parts by weight of paraffinic mineral oil (boiling range for example    about 255 to above 277° C.) and grinding the mixture in a ball mill    to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I), 75 parts by weight of    cyclohexanone as solvent and 10 parts by weight of oxyethylated    nonylphenol as emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I),        -   10 parts by weight of calcium lignosulphonate,        -   5 parts by weight of sodium laurylsulphate,        -   3 parts by weight of polyvinyl alcohol and        -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disc mill, and granulating the        powder in a fluidized bed by spray application of water as a        granulating liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting    -   25 parts by weight of a compound of the formula (I),    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulphonate,    -   2 parts by weight of sodium oleoylmethyltaurinate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water,    -   on a colloid mill, subsequently grinding the mixture in a bead        mill and atomizing and drying the resulting suspension in a        spray tower by means of a single-substance nozzle.

(C) BIOLOGICAL EXAMPLES 1. Herbicidal Pre-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantswere placed in wood-fibre pots in sandy loam and covered with soil. Thecompounds (I) according to the invention, formulated in the form ofwettable powders (WP), were then applied as aqueous suspension oremulsion at a water application rate of 600 I/ha (converted) with theaddition of 0.2% of wetting agent to the surface of the covering soil.

After the treatment, the pots were placed in a greenhouse and kept undergood growth conditions for the test plants. After about 3 weeks, theeffect of the preparations was scored visually in comparison withuntreated controls as percentages. For example, 100% activity=the plantshave died, 50% herbicidal activity or damage=the plants have beenreduced by 50% or the plant mass has been reduced by 50%, 0%activity=like control plants. Compounds (I) according to the inventionsuch as, for example, the compounds Nos. Iba1, Iba2, Iba3, Iba5, Iba7,Ibc8, Iba9, Iba11, Iba12, Iba13, Iba14, Iba18, Iba19, Iba23, Ibb23,erythro-Ibb1, threo-Ibb1, erythro-Ibd2, erythro-Ibe2, erythro-Ibb2,erythro-1-Ibb2, erythro-2-Ibb2, erythro-Ibc2, threo-Ibd2, threo-Ibe2,threo-1-Ibb2, threo-Ibb2, threo-2-Ibb2, threo-Ibc2, threo-Ibc3,erythro-Ibc3, erythro-Ibb3, threo-1-Ibb3, threo-2-Ibb3, threo-Ibb3,erythro-Ibb4, threo-Ibb4, erythro-Ibv5, erythro-Ibc5, erythro-Ibb5,erythro-1-Ibb5, erythro-2-Ibb5, threo-Ibb5, threo-1-Ibb5, threo-2-Ibb5,threo-Ibc5, threo-Ibv5, erythro-Ibb7, threo-Ibb7, erythro-Ibb8,erythro-Ibc8, threo-Ibb8, erythro-Ibb9, threo-Ibb9, threo-Ibc9,erythro-Ibb10, threo-Ibb10, erythro-Iba11, threo-Iba11, erythro-Iba12,threo-Iba12, threo-Ibb12, erythro-Ibb12, erythro-Ibb13, threo-Ibb13,erythro-Ibb14, threo-Ibb14, erythro-Ibb15, threo-Ibb15, erythro-Ibb17,threo-Ibb17, erythro-Ibb18, threo-Ibb18, erythro-Ibc19, threo-Ibc19,erythro-Ibb21, threo-Ibb21, erythro-Ibb32, threo-Ibb32, erythro-Ibb33,threo-Ibb33, erythro-Ibb34, threo-Ibb34, erythro-Ibb35, threo-Ibb35,threo-2-Ibb35, erythro-Ibb36, threo-Ibb36, threo-Ibb37, erythro-Ibb37,threo-1-Ibb37, threo-2-Ibb37, erythro-Ibb38, threo-Ibb38, erythro-Ibc43,threo-Ibc43, erythro-Ibb49, threo-Ibb49, erythro-Ibb50, threo-Ibb50,erythro-Ibb51, threo-Ibb51, erythro-Ibb55, threo-Ibb55, erythro-Ibb56,threo-Ibb56, erythro-Ibb75 and threo-Ibb75 from Tables 2 to 2f abovehave good herbicidal efficacy (70% to 100% activity) against a pluralityof harmful plants at an application rate of 320 g or less of activesubstance per hectare when applied by the pre-emergence method.

Here, for example, the compounds Nos. erythro-Ibe2, erythro-Ibc2,threo-Ibd2, threo-Ibe2, threo-Ibb2, threo-2-Ibb2, threo-Ibc3,erythro-Ibc3, erythro-Ibb3, threo-2-Ibb3, threo-Ibb3, erythro-Ibb4,threo-Ibb4, erythro-Ibc5, erythro-Ibb5, threo-Ibb5, threo-Ibc5,threo-Ibb8, threo-Ibb15, threo-Ibb17, erythro-Ibb36, threo-Ibc43,erythro-Ibb49, threo-Ibb49, erythro-Ibb50, threo-Ibb50, erythro-Ibb51and threo-Ibb56 have very good activity (90-100%) against harmful plantssuch as Echinochloa crus-galli when applied by the pre-emergence methodat an application rate of 0.32 kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibe2, threo-Ibd2, threo-Ibe2,threo-2-Ibb2, threo-Ibc2, threo-Ibc3, threo-2-Ibb3, threo-Ibb3,threo-Ibb4, threo-Ibb5, threo-Ibc5, threo-Ibb15, threo-Ibb17,erythro-Ibb35, threo-Ibb35 and threo-Ibc43 have good activity (80-100%)against harmful plants such as Setaria virides when applied by thepre-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

For example, the compounds Nos. threo-Ibb2, threo-2-Ibb3, threo-Ibb4,threo-Ibc5, threo-Ibb15, threo-Ibb35, threo-Ibb49 and threo-Ibb56 havevery good activity (80-100%) against harmful plants such as Veronicapersica when applied by the pre-emergence method at an application rateof 0.32 kg of active substance per hectare.

2. Herbicidal Post-Emergence Action

Seeds of monocotyledonous and dicotyledonous weed plants and crop plantswere placed in sandy loam in wood-fibre pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants were treated at the one-leaf stage, wherethe compounds (I) according to the invention, formulated in the form ofwettable powders (WP), were applied by spraying as aqueous suspension oremulsion at a water application rate of 600 I/ha (converted) with theaddition of 0.2% of wetting agent to the green parts of the plants.After the test plants had been kept in the greenhouse under optimumgrowth conditions for about 3 weeks, the activity of the preparationswas rated visually in comparison to untreated controls as percentages:For example, 100% activity=the plants have died, 50% herbicidal activityor damage=the plants have been reduced by 50% or the plant mass has beenreduced by 50%, 0% activity=like control plants.

As shown by the results, compounds (I) according to the invention suchas, for example, the compounds Nos. Iba1, Iba2, Iba3, Iba5, Iba7, Ibc8,Iba9, Iba11, Iba12, Iba13, Iba14, Iba18, Iba19, Iba23, Ibb23,erythro-Ibb1, threo-Ibb1, erythro-Ibd2, erythro-Ibe2, erythro-Ibb2,erythro-1-Ibb2, erythro-2-Ibb2, erythro-Ibc2, threo-Ibd2, threo-Ibe2,threo-1-Ibb2, threo-Ibb2, threo-2-Ibb2, threo-Ibc2, threo-Ibc3,erythro-Ibc3, erythro-Ibb3, threo-1-Ibb3, threo-2-Ibb3, threo-Ibb3,erythro-Ibb4, threo-Ibb4, erythro-Ibv5, erythro-Ibc5, erythro-Ibb5,erythro-1-Ibb5, erythro-2-Ibb5, threo-Ibb5, threo-1-Ibb5, threo-2-Ibb5,threo-Ibc5, threo-Ibv5, erythro-Ibb7, threo-Ibb7, erythro-Ibb8,erythro-Ibc8, threo-Ibb8, erythro-Ibb9, threo-Ibb9, threo-Ibc9,erythro-Ibb10, threo-Ibb10, erythro-Iba11, threo-Iba11, erythro-Iba12,threo-Iba12, threo-Ibb12, erythro-Ibb12, erythro-Ibb13, threo-Ibb13,erythro-Ibb14, threo-Ibb14, erythro-Ibb15, threo-Ibb15, erythro-Ibb17,threo-Ibb17, erythro-Ibb18, threo-Ibb18, erythro-Ibc19, threo-Ibc19,erythro-Ibb21, threo-Ibb21, erythro-Ibb32, threo-Ibb32, erythro-Ibb33,threo-Ibb33, erythro-Ibb34, threo-Ibb34, erythro-Ibb35, threo-Ibb35,threo-2-Ibb35, erythro-Ibb36, threo-Ibb36, threo-Ibb37, erythro-Ibb37,threo-1-Ibb37, threo-2-Ibb37, erythro-Ibb38, threo-Ibb38, erythro-Ibc43,threo-Ibc43, erythro-Ibb49, threo-Ibb49, erythro-Ibb50, threo-Ibb50,erythro-Ibb51, threo-Ibb51, erythro-Ibb55, threo-Ibb55, erythro-Ibb56,threo-Ibb56 and threo-Ibb75 from Tables 2 to 2f above have goodherbicidal efficacy (70% to 100% activity) against a plurality ofharmful plants at an application rate of 320 g or less of activesubstance per hectare when applied by the post-emergence method.

Here, for example, the compounds Nos. Iba2, Iba3, Iba5, threo-Ibb1,erythro-Ibd2, erythro-Ibb2, erythro-Ibc2, threo-Ibd2, threo-Ibe2,threo-Ibb2, threo-2-Ibb2, threo-Ibc2, threo-Ibc3, erythro-Ibc3,erythro-Ibb3, threo-2-Ibb3, threo-Ibb3, threo-Ibb4, erythro-Ibb5,erythro-2-Ibb5, threo-2-Ibb5, threo-Ibb5, threo-Ibc5, threo-Ibv5,threo-Ibb8, erythro-Ibb33, threo-Ibb33, threo-Ibb34, erythro-Ibb35,threo-2-Ibb35, threo-2-Ibb37, erythro-Ibb38, threo-Ibb38, erythro-Ibc43,threo-Ibc43, erythro-Ibb49, threo-Ibb49, threo-Ibb50, erythro-Ibb51 andthreo-Ibb51 from Tables 2 to 2f above have very good activity (80-100%)against harmful plants such as Echinochloa crus-galli when applied bythe post-emergence method at an application rate of 0.32 kg of activesubstance per hectare.

Here, for example, the compounds Nos. Ibc8, Iba23, Ibb23, threo-Ibb1,threo-Ibe2, threo-Ibb2, threo-2-Ibb2, erythro-Ibc2, threo-Ibc2,erythro-Ibc5, threo-Ibb5, threo-2-Ibb5, threo-Ibc5, threo-Ibb8,threo-Ibb12, threo-Ibb14, erythro-Ibb32, threo-Ibb32, threo-Ibb33,erythro-Ibb34, threo-Ibb34, threo-Ibb37 and threo-Ibc43 have goodactivity (80-100%) against harmful plants such as Polygonum convulvuswhen applied by the post-emergence method at an application rate of 0.32kg of active substance per hectare.

For example, the compounds Nos. erythro-Ibb2, erythro-Ibc2, threo-Ibd2,threo-Ibe2, threo-Ibb2, threo-Ibc2, threo-Ibc3, threo-Ibb3, threo-Ibb5,threo-2-Ibb5, threo-Ibc5, threo-Ibb37, erythro-Ibb49 and threo-Ibb49also have good activity (80-100%) against harmful plants such as Setariavirides when applied by the post-emergence method at an application rateof 0.32 kg of active substance per hectare.

1. A Compound of the formula (I) and/or salt thereof

in which R¹ represents hydrogen or a hydrolysable radical, (R²)_(n)represents n substituents R², where R², if n=1, or each of thesubstituents R², if n is greater than 1, independently of the othersrepresents halogen, cyano, nitro, hydroxy, (C₁-C₈)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₈)-alkoxy, (C₁-C₈)-alkylthio,(C₁-C₈)-alkylsulphinyl, (C₁-C₈)-alkylsulphonyl, (C₁-C₆)-halo alkyl,(C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulphinyl,(C₁-C₆)-haloalkylsulphonyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,(C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy,(C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy,(C₃-C₆)-cycloalkyl which is optionally substituted by one or moreradicals from the group consisting of halogen and (C₁-C₄)-alkyl,(C₃-C₆)-cycloalkoxy which is optionally substituted by one or moreradicals from the group consisting of halogen and (C₁-C₄)-alkyl, or aradical of the formula C(O)OR³, C(O)NR⁴R⁵, C(O)—Het², NR⁶R⁷ or Het³ orwhere in each case two groups R² located ortho at the ring together area group of the formula -Z¹-A**-Z² in which A** represents an alkylenegroup having 1 to 4 carbon atoms which is optionally substituted by oneor more radicals from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-halo alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z¹ representsa direct bond, O or S and Z² represents a direct bond, O or S, where thegroup -Z¹-A**-Z² together with the carbon atoms, attached to the group,of the phenyl ring form a fused-on 5- or 6-membered ring, R³ representshydrogen, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl or the group M mentioned below, R⁴, R⁵, R⁶ and R⁷independently of one another each represent hydrogen, (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, where each of the 3 last-mentionedradicals in each case independently of the others is unsubstituted orsubstituted by one or more radicals from the group consisting ofhalogen, nitro, cyano and phenyl which is optionally substituted, or(C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentionedradicals in each case independently of the other is unsubstituted orsubstituted by one or more radicals from the group consisting ofhalogen, nitro, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl andbenzyl, where each of the 2 last-mentioned radicals is optionallysubstituted, Het¹ independently of the others in each case represents asaturated, partially unsaturated or heteroaromatic monocyclicheterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-memberedbicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms selectedfrom the group consisting of O, N and S, Het² and Het³ independently ofone another each represent a saturated or partially unsaturated radicalof a heterocycle having 3 to 9 ring atoms and at least one nitrogen atomas ring heteroatom at position 1 of the ring and optionally 1, 2 or 3further ring heteroatoms from the group consisting of N, O and S, wherethe radical of the heterocycle at the nitrogen atom in position 1 of thering is attached to the remainder of the molecule of the compound of theformula (I) and where the heterocycle is unsubstituted or substituted byone or more radicals from the group consisting of halogen,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio and oxo, R*, R** independently of one another (andalso independently of other radicals NR*R**) each represent H,(C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,[(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,[(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkylcarbonyl, phenyl, phenylcarbonyl,phenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkylcarbonyl, where each of the 7last-mentioned radicals is optionally substituted in the cycle by one ormore identical or different radicals from the group consisting ofhalogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and(C₁-C₄)-haloalkoxy or, in the case of saturated cyclic base groups, alsooxo, or R* and R** together with the nitrogen atom represent a 3- to8-membered heterocycle which, in addition to the nitrogen atom, maycontain one or two further ring heteroatoms from the group consisting ofN, O and S and which is unsubstituted or substituted by one or moreradicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyland oxo, R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₈)-alkyl,(C₁-C₆)-haloalkyl, cyano-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkyl,nitro-(C₁-C₆)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl,(C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy,(C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy,(C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy,(C₁-C₈)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,(C₁-C₈)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,(C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of theformula R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)-alkyl, the radicals R^(aa)being defined further below, —NR*R**, R* and R** being defined furtherbelow, tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,(C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy,(C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy,phenyl, phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl,phenylamino, phenylamino-(C₁-C₈)-alkyl or a 5- or 6-membered monocyclicor 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4heteroatoms selected from the group consisting of O, N and S, where eachof the 11 last-mentioned radicals is optionally substituted in thecyclic moiety by one or more identical or different radicals R^(bb),R^(aa) independently of one another each represent hydrogen, OH,(C₁-C₈)-alkyl, (C₁-C₆)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,(C₁-C₈)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkoxy,(C₃-C₈)-alkenyloxy, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkyl,(C₃-C₈)-alkenyloxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkynyloxy,(C₃-C₈)-alkynyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkoxy,—NR*R*, where R* and R** are as defined above, tri-[(C₁-C₄)-alkyl]silyl,tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl,(C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₈)-cycloalkenyl,(C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkenyloxy,(C₅-C₈)-cycloalkynyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl,(C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl,phenyl-(C₁-C₈)-alkoxy, phenoxy, phenoxy-(C₁-C₈)-alkyl,phenoxy-(C₁-C₈)-alkoxy, phenylamino, phenylamino-(C₁-C₈)-alkyl,phenylamino-(C₁-C₈)-alkoxy or a 5- or 6-membered monocyclic or 9- or10-membered bicyclic heterocycle which is optionally attached via analkylene group or an alkoxy group and contains 1, 2, 3 or 4 heteroatomsselected from the group consisting of O, N and S, where each of thelast-mentioned radicals is optionally substituted in the cyclic moietyby one or more identical or different radicals R^(cc), and R^(bb) andR^(cc) independently of one another each represent halogen,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxyor, in the case of saturated or partially unsaturated cyclic basegroups, also represent oxo and M represents an equivalent of a cation, nrepresents 1, 2, 3, 4 or
 5. 2. Compound and/or salt thereof according toclaim 1, wherein R¹ represents hydrogen or an optionally substitutedhydrocarbon radical or an optionally substituted heterocyclyl radical,where each of the two last-mentioned carbon-containing radicalsincluding substituents has 1 to 30 carbon atoms, optionally 1 to 24carbon atoms, 1 to 20 carbon atoms, or R¹ represents a radical of theformula SiR^(a)R^(b)R^(c), —NR^(a)R^(b) or —N═CR^(c)R^(d), where in the3 last-mentioned formulae each of the radicals R^(a), R^(b), R^(c) andR^(d) independently of the others represents hydrogen or an optionallysubstituted hydrocarbon radical, where, however, SiH₃ forSiR^(a)R^(b)R^(c) is excluded, or R^(a) and R^(b) together with thenitrogen atom of the group —NR^(a)R^(b) represent a 3- to 9-memberedheterocycle which, in addition to the nitrogen atom, may contain one ortwo further ring heteroatoms from the group consisting of N, O and S andwhich is unsubstituted or substituted, or R^(c) and R^(d) together withthe carbon atom of the group —N═CR^(c)R^(d) represent a 3- to 9-memberedcarbocyclic radical or a heterocyclic radical which may contain 1 to 3ring heteroatoms from the group consisting of N, O and S, where thecarbocyclic or heterocyclic radical is unsubstituted or substituted,where each of the radicals R^(a), R^(b), R^(e) and R^(d) includingsubstituents has up to 30 carbon atoms, or R¹ represents a radical ofthe formula —C(═O)—R^(e) or —P(═O)(R^(f))₂ where R^(e) and R^(f)independently of one another each represent hydrogen, OH, (C₁-C₈)-alkyl,(C₁-C₄)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₈)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₈)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-haloalkoxy-(C₁-C₈)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₈)-alkoxy, (C₃-C₈)-alkenyloxy,(C₃-C₈)-alkenyloxy-(C₁-C₈)-alkyl, (C₃-C₈)-alkenyloxy-(C₁-C₈)-alkoxy,(C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₈)-alkyl,(C₃-C₈)-alkynyloxy-(C₁-C₈)-alkoxy, —NR*R**, where R* and R** are definedfurther below, tri-[(C₁-C₄)-alkyl]silyl,tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₈)-alkyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cyclo alkyl-(C₁-C₈)-alkyl, (C₃-C₆)-cycloalkyl-(C₁-C₈)-alkoxy,(C₅-C₆)-cycloalkenyl, (C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkyl,(C₅-C₆)-cycloalkenyl-(C₁-C₈)-alkoxy, (C₅-C₆)-cycloalkynyl,(C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkyl, (C₅-C₆)-cycloalkynyl-(C₁-C₈)-alkoxy,phenyl, phenyl-(C₁-C₈)-alkyl, phenyl-(C₁-C₈)-alkoxy, phenoxy,phenoxy-(C₁-C₈)-alkyl, phenoxy-(C₁-C₈)-alkoxy, phenylamino,phenylamino-(C₁-C₈)-alkyl, phenylamino-(C₁-C₈)-alkoxy, a radical Het¹,Het¹-(C₁-C₆)-alkyl, Het¹(C₁-C₆)-alkoxy, Het¹-O—(C₁-C₆)-alkyl orHet¹-O—(C₁-C₆)-alkoxy, where each of the 23 last-mentioned radicals isunsubstituted in the acyclic moiety or substituted by one or moreidentical or different radicals R^(A) and is unsubstituted in the cyclicmoiety or substituted by one or more identical or different radicalsR^(B), Het¹ independently of the others in each case represents asaturated, partially unsaturated or heteroaromatic monocyclicheterocyclyl radical having 3 to 9 ring atoms or a 9- or 10-memberedbicyclic heterocycle, each containing 1, 2, 3 or 4 heteroatoms selectedfrom the group consisting of O, N and S, R*, R** independently of oneanother (and also independently of other radicals NR*R**) each representH, (C₁-C₈)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkanoyl,[(C₁-C₄)-haloalkyl]carbonyl, [(C₁-C₄)-alkoxy]carbonyl,[(C₁-C₄)-haloalkoxy]carbonyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl-(C₁-C₄)-alkylcarbonyl, phenyl, phenylcarbonyl,phenyl-(C₁-C₄)-alkyl, phenyl-(C₁-C₄)-alkylcarbonyl, where each of the 7last-mentioned radicals is optionally substituted in the cycle by one ormore identical or different radicals from the group consisting ofhalogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and(C₁-C₄)-haloalkoxy or, in the case of saturated cyclic base groups, alsooxo, or R* and R** together with the nitrogen atom represent a 3- to8-membered heterocycle which, in addition to the nitrogen atom, maycontain one or two further ring heteroatoms from the group consisting ofN, O and S and which is unsubstituted or substituted by one or moreradicals from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyland oxo, R^(A) represents halogen, cyano, hydroxy or (C₁-C₆)-alkoxy,R^(B) represents halogen, cyano, hydroxy, oxo, nitro, (C₁-C₈)-alkyl,(C₁-C₆)-haloalkyl, cyano-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkyl,nitro-(C₁-C₆)-alkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-haloalkenyl,(C₂-C₈)-alkynyl, (C₂-C₈)-haloalkynyl, (C₁-C₈)-alkoxy,(C₂-C₈)-alkenyloxy, (C₂-C₈)-alkynyloxy, (C₁-C₈)-haloalkoxy,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-alkoxy,(C₁-C₆)-haloalkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-haloalkoxy-(C₁-C₄)-alkoxy,(C₁-C₈)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio,(C₁-C₈)-alkylsulphinyl, (C₁-C₆)-haloalkylsulphinyl,(C₁-C₈)-alkylsulphonyl, (C₁-C₆)-haloalkylsulphonyl, a radical of theformula R^(aa)—C(═O)—, R^(aa)—C(═O)—(C₁-C₆)-alkyl, the radicals R^(aa)being defined further below, —NR*R**, R* and R** being defined furtherbelow, tri-[(C₁-C₄)-alkyl]silyl, tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,(C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, phenyl,phenyl-(C₁-C₈)-alkyl, phenoxy, phenoxy-(C₁-C₈)-alkyl, phenylamino,phenylamino-(C₁-C₈)-alkyl or a 5- or 6-membered monocyclic or 9- or10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatomsselected from the group consisting of O, N and S, where each of the 11last-mentioned radicals is optionally substituted in the cyclic moietyby one or more identical or different radicals R^(bb), R^(aa)independently of one another each represent hydrogen, OH, (C₁-C₈)-alkyl,(C₁-C₆)-haloalkyl, (C₂-C₈)-alkenyl, (C₂-C₈)-alkynyl, (C₁-C₈)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyloxy,(C₁-C₆)-haloalkoxy, (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxy-(C₁-C₆)-alkoxy, (C₃-C₈)-alkenyloxy,(C₃-C₈)-alkenyloxy-(C₁-C₆)-alkyl, (C₃-C₈)-alkenyloxy-(C₁-C₆)-alkoxy,(C₃-C₈)-alkynyloxy, (C₃-C₈)-alkynyloxy-(C₁-C₆)-alkyl,(C₃-C₈)-alkynyloxy-(C₁-C₆)-alkoxy, —NR*R*, where R* and R** are asdefined above, tri-[(C₁-C₄)-alkyl]silyl,tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkyl,tri-[(C₁-C₄)-alkyl]silyl-(C₁-C₆)-alkoxy, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₈)-alkyl,(C₃-C₈)-cycloalkyl-(C₁-C₈)-alkoxy, (C₅-C₈)-cycloalkenyl,(C₅-C₈)-cycloalkenyl-(C₁-C₆)-alkyl, (C₅-C₈)-cycloalkenyloxy,(C₅-C₈)-cycloalkynyl, (C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkyl,(C₅-C₈)-cycloalkynyl-(C₁-C₆)-alkoxy, phenyl, phenyl-(C₁-C₈)-alkyl,phenyl-(C₁-C₈)-alkoxy, phenoxy, phenoxy-(C₁-C₈)-alkyl,phenoxy-(C₁-C₈)-alkoxy, phenylamino, phenylamino-(C₁-C₈)-alkyl,phenylamino-(C₁-C₈)-alkoxy or a 5- or 6-membered monocyclic or 9- or10-membered bicyclic heterocycle which is optionally attached via analkylene group or an alkoxy group and contains 1, 2, 3 or 4 heteroatomsselected from the group consisting of O, N and S, where each of thelast-mentioned radicals is optionally substituted in the cyclic moietyby one or more identical or different radicals R^(cc), and R^(bb) andRCC independently of one another each represent halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxy or, in the caseof saturated or partially unsaturated cyclic base groups, also representoxo and M represents an equivalent of a cation.
 3. Compound and/or saltthereof according to claim 1, wherein R¹ represents H, (C₁-C₁₈)-alkyl,(C₂-C₁₈)-alkenyl or (C₂-C₁₈)-alkynyl, where each of the 3 last-mentionedradicals is unsubstituted or substituted and, including substituents,has up to 30 carbon atoms, or represents (C₃-C₉)-cycloalkyl,(C₅-C₉)-cycloalkenyl, (C₅-C₉)-cycloalkynyl or phenyl, where each of the4 last-mentioned radicals is unsubstituted or substituted and, includingsubstituents, has up to 30 carbon atoms.
 4. Compound and/or salt thereofaccording to claim 1, wherein (R²)_(n) represents n substituents R²,where R², if n=1, or each of the substituents R², if n is greater than1, independently of the others represents halogen, cyano, nitro,hydroxy, (C₁-C₆)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulphinyl,(C₁-C₆)-alkylsulphonyl, (C₁-C₄)-halo alkyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulphinyl,(C₁-C₄)-haloalkylsulphonyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-haloalkynyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl which is optionally substituted by one or moreradicals from the group consisting of halogen and (C₁-C₄)-alkyl,(C₃-C₆)-cycloalkoxy which is optionally substituted by one or moreradicals from the group consisting of halogen and (C₁-C₄)-alkyl, or aradical of the formula C(O)OR³, C(O)NR⁴R⁵, C(O)—Het², NR⁶R⁷ or Het³ orwhere in each case two groups R² located ortho at the ring together area group of the formula -Z¹-A**-Z² in which A** represents an alkylenegroup having 1 to 4 carbon atoms which is optionally substituted by oneor more radicals from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-halo alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Z¹ representsa direct bond, O or S and Z² represents a direct bond, O or S, where thegroup -Z¹-A**-Z² together with the carbon atoms, attached to the group,of the phenyl ring form a fused-on 5- or 6-membered ring, R³ representshydrogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-halocycloalkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl,(C₂-C₄)-alkynyl or the group M mentioned, R⁴, R⁵, R⁶ and R⁷independently of one another each represent hydrogen or (C₁-C₄)-alkylwhich is unsubstituted or substituted by one or more radicals from thegroup consisting of halogen, nitro, cyano and phenyl, or(C₃-C₆)-cycloalkyl or phenyl, where each of the 2 last-mentionedradicals in each case independently of the other is unsubstituted orsubstituted by one or more radicals from the group consisting ofhalogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, phenyl and benzyl, Het² andHet³ independently of one another each represent a saturated orpartially unsaturated radical of a heterocycle having 3 to 6 ring atomsand at least one nitrogen atom as ring heteroatom at position 1 of thering and optionally 1, 2 or 3 further ring heteroatoms from the groupconsisting of N, O and S, where the radical of the heterocycle isattached at the nitrogen atom in position 1 of the ring to the remainderof the molecule of the compound of the formula (I) and where theheterocycle is unsubstituted or substituted by one or more radicals fromthe group consisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl andoxo, optionally the radical of a saturated heterocycle of the typementioned, optionally a morpholino, piperidino or pyrrolidino group, andn represents 1, 2, 3, 4 or
 5. 5. Compound and/or salt thereof accordingto claim 1, wherein (R²)_(n) represents n substituents R², where R², ifn=1, or each of the substituents R², if n is greater than 1,independently of the others represents halogen, cyano, nitro, methyl,ethyl, methoxy, ethoxy, methylthio, ethylthio, (C₁-C₂)-alkylsulphinyl,(C₁-C₂)-alkylsulphonyl, (C₁-C₂)-haloalkyl, (C₁-C₂)-haloalkoxy,(C₁-C₂)-haloalkylthio, (C₁-C₂)-haloalkylsulphinyl,(C₁-C₂)-haloalkylsulphonyl or (C₁-C₂)-alkoxy-(C₁-C₂)-alkyl, and nrepresents 1, 2, 3, 4 or
 5. 6. Compound and/or salt thereof according toclaim 1, wherein (R²)_(n) represents n substituents R², where R², ifn=1, or each of the substituents R², if n is greater than 1,independently of the others represents halogen, optionally comprisingfluorine, chlorine, bromine or iodine, or cyano, nitro, methyl, methoxy,methylthio, methylsulphinyl, methylsulphonyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoroalkylthio,trifluoromethylsulphinyl or trifluoromethylsulphonyl, and n represents1, 2, 3, 4 or
 5. 7. Process for preparing a compound of formula (I) asdefined in claim 1 and/or a salt thereof, comprising reacting (a) acompound of the formula (II)

with a compound of the formula (III) or a salt thereof

to give the compound of the formula (I)

where R¹, R² and n in the compounds (II) and (III) are as defined in therespective compound of the formula (I) to be prepared, (b) a compound ofthe formula (I*),

in which R is a radical from the group of the radicals possible for R¹,but different from the radical R¹ in the compound (I) to be prepared, isreacted with a compound of the formula R¹—OH, in which R¹ is defined asin formula (I), to give the compound (I), where R² and n in the compound(I*) are as defined in the respective compound of the formula (I) to beprepared, (c) a compound of the formula (I*) mentioned under (b) inwhich the radical R represents hydrogen is esterified with an alcohol ofthe formula R¹—OH by customary methods, where R² and n in the compound(I*) are as defined in the respective compound of the formula (I) to beprepared, (d) in the case of the preparation of an optically activecompound of a diastereomeric form of the compound of the formula (I),the racemic mixture of the diastereomeric form of the compound of theformula (I) is subjected to an optical resolution and the desiredenantiomer is isolated in a stereochemical purity of from 60 to 100%,based on the mixture of the erythro or threo enantiomers present. 8.Herbicidal and/or plant-growth-regulating composition, comprising one ormore compounds as defined in claim 1 and one or more formulationauxiliaries customary in crop protection.
 9. Method for controlling oneor more harmful plants and/or for regulating the growth of plants,comprising applying an effective amount of one or more compounds asdefined in claim 1 onto a plants, plant seed, soil in which or on whichplants grow and/or an area under cultivation.
 10. Method according toclaim 9, wherein the compound of the formula (I) and/or salt thereof isemployed for selective control of one or more harmful plants and/or forregulating growth in one or more crops of useful plants and/orornamentals.
 11. A compound of formula (I) and/or a salt thereofaccording to claim 1 capable of being used as a herbicide and/or plantgrowth regulator.